• 专利附录
  • 专利说明
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    • 专利摘要:
    Procedure for obtaining pdi derivatives. The present invention relates to a process for the preparation of perylenediimide derivatives of formula i where the meaning for r1, r2 and r3 is the one indicated in the description. These compounds are useful for the preparation of dyes, pigments, paints, fluorescent agents, optical devices, electronic devices, electro-optical devices, light-emitting diodes and organic or hybrid photovoltaic cells. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2558260A1
    申请号:ES201431181
    申请日:2014-08-01
    公开日:2016-02-02
    发明作者:Fernando FERNÁNDEZ LÁZARO；Nathalie ZINK LORRE；Enrique FONT SANCHIS；David GUTIÉRREZ MORENO；Ángela SASTRE SANTOS
    申请人:Universidad Miguel Hernandez de Elche；
    IPC主号:
    专利说明:

    The present invention relates to a process for preparing derivatives ofperylenediimide of formula I, characterized by being substituted in positions 1,6, 7 and / or 12 (bay positions).
    STATE OF THE TECHNIQUE
    10 Perimin-3,4,9,10-tetracarboxylic acid diimides, also known as perylenediimides (PDI) or as perylene bisimides (PBI), are very stable compounds both chemically and thermally, and also against electromagnetic radiation. The POIs absorb intensely in the ultraviolet-visible region of the electromagnetic spectrum, so they exhibit very vivid colorations that, depending on the
    15 substituents that present, can vary from orange to blue, through red and green. The POIs are highly fluorescent, with quantum fluorescence yields that can reach the unit. Other properties of IDPs include their high electronic affinity and their great ability to transport electrons under the influence of an electric field. For all these characteristics, they are used
    20 widely in the industry as dyes, pigments in paints and fluorescent agents. They are also used in research for the development of optical, electronic and electro-optical devices such as field effect transistors, light emitting diodes and photovoltaic devices (solar cells).
    25 The optical, electronic and electro-optical properties of IDPs can be modified depending on the substituents. Important changes in the properties are obtained by introducing, modifying or varying the substituents on the bay positions (1, 6, 7 and / or 12) of the POI. The introduction on the bay positions (1, 6, 7 and / or 12) of Oalkyl and O-aryl groups, linked to the PDI by the oxygen atom, and azacycloalkanes, attached to
    30 the PDI for the nitrogen atom, has been widely used.
    The O- or N-substituted POIs in the bay positions are obtained in two stages. The first is to halogenate (chlorinate or brominate) the unsubstituted PDI. The POI (usually with chlorine) can be tetrahalogenated at positions 1, 6, 7 and 12. On the other hand, the PDI (usually with bromine) can be dihalogenated to obtain a mixture


    of two regioisomers, 1,6-dibromoPDI (minor isomer) and 1,7-dibromoPDI (majority isomer), which cannot be separated by standard techniques.
    In a second stage the halogen atoms (chlorine or bromine) are replaced by
    5 reaction in basic medium, with alcoholates, phenolates or amines. In the case of IDPsdisubstituted, the mixture of isomers 1.6 (minority) and 1.7 is still maintained(majority), although in some cases they can be separated by techniqueschromatographic
    10 These and other properties and characteristics of IDPs are found in many monographs and scientific articles, such as (a) F. Würthner. Chem. Commun. 2004, 1564-1579. (b) H. Langhals. Helv. Chim. Minutes 2005, 88, 1309-1343.
    (c) A. Herrmann, K. Müllen. Chem. Lett. 2006, 35, 978-985. (d) F. Würthner. Pure Appl. Chem. 2006, 78, 2341-2349. (e) C. Huang, S. Barlow, S. R. Marder. J. Org.
    15 Chem. 2011, 76, 2386-2407. (f) X. Zhan, A. Facchetti, S. Barlow, T. J. Marks, M. A. Ratner, M. R. Wasielewski, S. R. Marder. Adv. Mater. 2011, 23, 268-284. (g) C. Li, H. Wonneberger. Adv. Mater. 2012, 24, 613-636.
    Therefore, these procedures have to be carried out in at least two stages, of
    20 which one corresponds to a halogenation (chlorination or bromination) of the POIs to functionalize the positions that can be substituted. On the other hand, by means of the procedures described, only monosubstituted, disubstituted POIs (as a mixture of regioisomers, where the isomer 1.7 over 1.6) and tetrasubstituted isomers can be obtained.
    Thus, it would be desirable to have an alternative, more selective and more efficient method, which would facilitate obtaining in one stage the substituted PDI compounds. It would also be desirable for the method to allow, in addition to monosubstituted POIs, disubstituted POIs in which the 1,6 isomer was higher
    30 proportion Finally, a method would be needed that would make it possible to obtain the 1.12 isomer and trisubstituted PDI.
    DESCRIPTION OF THE INVENTION
    The present invention relates to a process for preparing the compounds of formula I:


    where:each R1 and R3 independently represent hydrogen, halogen, C1-C20 alkyl,C2-C20 alkenyl, C2-C20 alkynyl, -CN, -COR4, -CO2R4, -CONR4R4, -OR4, -OCOR4,
    5 -OCONR4R4, -OCO2R4, -SR4, -SeR4, -NR4R4, -NR4COR4, -NR4CONR4R4, -NR4CO2R4, -PR4R4, -SOR4, -SO2R4, -SO2NR4R4 or Cy1, where C1-C20 to C1-C20 alkyl C2-C20 alkynyl are independently optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl or Cy2; where C1-C40 alkyl
    10 is optionally substituted by one or more R5 and where Cy2 is optionally substituted by one or more R7; each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20 alkyl is optionally substituted by one or more R10 and where Cy4 is optionally substituted by one or more R11;
    15 or two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a heteroatom selected from N, O and S, and which may be optionally substituted by one or two R11; each R5 independently represents Cy3, -OR8, -SR8 or -NR8R8, where Cy3 is optionally substituted by one or more R6;
    Each R7 independently represents C1-C40 alkyl, Cy4, -OR8, -SR8 or -NR8R8, where C1-C40 alkyl is optionally substituted by one or more R9 and where Cy4 is optionally substituted by one or more R6; each R8 independently represents hydrogen, C1-C6 alkyl or Cy3, where C1-C6 alkyl is optionally substituted by one or more -OH, -OC1-C4 alkyl, where
    C1-C4 alkyl is optionally substituted by one or more -OH and where Cy3 is optionally substituted by one or more C1-C6 alkyl;


    each R6 and R11 independently represent R8, -OR8, -SR8 or -NR8R8;each R9 and R10 independently represent -OR8, -SR8, –NR8R8 or Cy3, where Cy3is optionally substituted by one or more C1-C6 alkyl;each Cy1 and Cy3 independently represent phenyl or an aromatic heterocycle of
    5 5 or 6 members containing 1 to 3 heteroatoms selected from N, O, S and Se, and where each Cy1 and Cy3 can be independently linked to the rest of the molecule through any available C or N atom; each Cy2 independently represents a saturated, partially unsaturated ring
    or aromatic, monocyclic 3 to 7 members or bicyclic 6 to 11 members that can
    10 being carbocyclic or heterocyclic, where Cy2 can be attached to the rest of the molecule through any available C or N atom, where Cy2 contains 1 to 4 heteroatoms selected from N, O, S and Se, and where one or more C, S or Se atoms of Cy2 may optionally be oxidized forming CO, SO, SO2, SeO or SeO2 groups; Y
    Each Cy4 independently represents a saturated carbocyclic or heterocyclic ring, partially unsaturated or aromatic of 3 to 7 members, optionally containing from 1 to 4 heteroatoms selected from N, O, S and Se, where Cy4 is attached to the rest of the molecule a through any available C or N atom, and where one or more C, S or Se atoms of Cy4 may optionally be oxidized
    20 forming groups CO, SO, SO2, SeO or SeO2, with the proviso that at least one R3 independently represents -OR4, -SR4, -SeR4, -NR4R4 or -PR4R4, which comprises reacting a compound of formula II with a compound of formula III in the presence of a source of fluorine:
    R1
    R12 R12
    R1
    R13-H R2
    II III
    where:


    each R1 and R2 independently have the meaning described for a compound of formula I; Each R12 independently represents hydrogen, halogen, -CN, -COR4, -CO2R4, -CONR4R4, -OR4, -OCOR4, -OCONR4R4, -OCO2R4, -SR4, -SeR4, -NR4R4, -NR4COR4,
    5 -NR4CONR4R4, -NR4CO2R4, -PR4R4, -SOR4, -SO2R4 or -SO2NR4R4; R13 represents –OR4, -SR4, -SeR4, -NR4R4 or -PR4R4; and each R4 independently has the meaning described for a compound of formula I, with the proviso that at least one R12 independently represents hydrogen or
    10 halogen.
    Another aspect of the present invention relates to a compound selected from:
    ,,,


    , Y
    Another aspect of the present invention relates to the use of a compound selected from:
    OR NOT
    N
    N
    N
    N
    N
    OR NOT
    24 25 5 , , ,


    , or, for the preparation of dyes, pigments, paints, fluorescent agents, optical devices, electronic devices, electro-optical devices, light emitting diodes and organic or hybrid photovoltaic cells.
    Throughout the present invention "C1-C40 alkyl", "C1-C20 alkyl", "C1-C6 alkyl" and "C1-C4 alkyl", as a group or part of a group, independently refer to a group straight or branched chain alkyl containing from 1 to 40, from 1 to 20, from 1 to 6 and from 1 to 4 C atoms respectively. "C1-C4 alkyl" includes methyl groups,
    Ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl; "C1-C6 alkyl" includes the groups of "C1-C4 alkyl" and, among others, pentyl iso-pentyl, sec-pentyl, neo-pentyl, 1,2-dimethylpropyl, hexyl, iso-hexyl and sec-hexyl; "C1-C20 alkyl" includes the groups of "C1-C6 alkyl" and, among others, heptyl, iso-heptyl, octyl, iso-octyl, 2-ethylhexyl, decyl, nonyl and dodecyl, 2-propylheptyl, 2-butylnonyl and 3-butylnonyl; "C1-C40 alkyl" includes
    15 "C1-C20 alkyl" groups and, among others, tridecyl and tetradecyl.
    A "C2-C20 alkenyl" group means a linear or branched alkyl chain containing from 2 to 20 C atoms, and which also contains one or more double bonds. Examples include, among others, the groups ethenyl, 1-propenyl, 2-propenyl,
    Isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 3-pentenyl, 5pentenyl, 2-hexenyl, 2,4-hexadienyl and 2-propyl-2-hexenyl.
    A "C2-C20 alkynyl" group means a linear or branched alkyl chain containing from 2 to 20 C atoms, and which also contains one or more triple bonds.


    Examples include the ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1,3-butadiinyl groups.
    Cy1 and C3 independently refer to a phenyl or a heteroaryl of 5 or 6
    5 members containing 1 to 3 heteroatoms selected from N, O, S and Se. Cy1 and C3 bind to the rest of the molecule through any C or N atom of the available ring. In addition, Cy1 and C3 may be optionally substituted as indicated in the definition of formula I, the substituents may be the same or different and may be located in any available position of the system of
    10 rings Examples include, among others, phenyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl.
    Cy2 refers to a monocyclic ring of 3 to 7 members or bicyclic of 6 to 11 members that can be carbocyclic or heterocyclic. When it is heterocyclic, it can contain 1 to 4 heteroatoms selected from N, O, S and Se. The bicyclic rings can be formed by two fused rings through two adjacent C or N atoms, or through two non-adjacent C or N atoms forming a ring with
    20 bridge, or they can be formed by two rings joined through a single C atom forming a ring of the Spieran type. The Cy2 group can be saturated, partially unsaturated or aromatic. Cy2 can be attached to the rest of the molecule through any available C or N atom. In Cy2 one or more atoms of C, S or Se of Cy2 may optionally be oxidized forming groups CO, SO, SO2, SeO
    25 or SeO2. In addition, Cy2 may be optionally substituted as indicated in the definition of a compound of formula I, if substituted, the substituents may be the same or different and may be located at any available position of the ring system. Examples include, among others, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, azetidinyl, aziridinyl, oxyranyl, oxetanyl, imidazolidinyl,
    30 isothiazolidinyl, isoxazolidinyl, oxazolidinyl, pyrazolidinyl, pyrrolidinyl, thiazolidinyl, dioxanyl, morpholinyl, thiomorpholinyl, 1,1-dioxothiomorpholinyl, piperazinyl, homopiperazinyl, piperidinyl, pyranyl, tetrahydropyranyl, homopiperidinyl, oxazinyl, oxazolinyl, pyrrolinyl, thiazolinyl, pyrazolinyl, imidazolinyl, isoxazolinyl , isothiazolinyl, 2-oxo-pyrrolidinyl, 2-oxo-piperidinyl, 4-oxo-piperidinyl, 2-oxo-piperazinyl, 2-oxo-1,2
    Dihydropyridyl, 2-oxo-1,2-dihydropyrazinyl, 2-oxo-1,2-dihydropyrimidinyl, 3-oxo-2,3-dihydropyridazyl, phenyl, naphthyl, thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl,


    isoxazolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, 1,3,4oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,2, 4-thiadiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzimidazolyl, benzooxazolyl, benzofuranyl, isobenzofuranyl, indolyl, isoindolyl, benzothiophenyl, benzothiazolyl, quinolinyl, 5 isoquinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, indazolyl, imidazopyridinyl, pyrrolopyridinyl, thienopyridinyl , imidazopyrimidinyl, imidazopyrazinyl, imidazopyridazinyl, pyrazolopyrazinyl, pyrazolopyridinyl, pyrazolopyrimidinyl, benzo [1,3] dioxolyl, phthalimidyl, 1-oxo-1,3-dihydroisobenzofuranyl, 1,3-dioxo-1,3-dihydro-2,3-dihydroisoyl -dihydro-1H-indolyl, 1-oxo-2,3-dihydro-1H-isoindolyl,
    10 perhydroquinolinyl, 1-oxo-perhydroisoquinolinyl, 1-oxo-1,2-dihydroisoquinolinyl, 4-oxo3,4-dihydroquinazolinyl, 2-aza-bicyclo [2.2.1] heptanyl, 5-aza-bicyclo [2.1.1] hexanyl , 2Hespiro [benzofuran-3,4'-piperidinyl], 3H-spiro [isobenzofuran-1,4'-piperidinyl], 1-oxo2,8-diazaspiro [4.5] decanyl and 1-oxo-2,7-diazaspiro [4.5 ] decanyl.
    15 In the above definition of Cy2, when the specified examples refer to a bicyclic ring in general terms, all possible arrangements of atoms are included.
    Cy4 represents a 3 to 7 member ring, saturated, partially unsaturated or
    20 aromatic, which can be carbocyclic or heterocyclic. If it is heterocyclic, it contains 1 to 4 heteroatoms selected from N, O, S and Se, which can be optionally oxidized to form CO, SO, SO2, SeO or SeO2 groups. Cy4 binds to the rest of the molecule through any available C or N atom. In addition, Cy4 may be optionally substituted as indicated in the definition of a
    The compound of formula I, if substituted, the substituents may be the same or different and may be located at any available position of the ring system. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, azetidinyl, aziridinyl, oxyranyl, oxetanyl, imidazolidinyl, isothiazolidinyl, isoxazolidinyl, oxazolidinyl, pyrazolidinyl, pyrrolidinyl, thiazolidyl, dioxidyl
    30 morpholinyl, thiomorpholinyl, 1,1-dioxothiomorpholinyl, piperazinyl, homopiperazinyl, piperidinyl, pyranyl, tetrahydropyranyl, homopiperidinyl, oxazinyl, oxazolinyl, pyrrolinyl, thiazolinyl, pyrazolinyl, imidazolinyl, isoxazolinyl, isothiazolinyl, 2-oxo-pyrrolidinyl, phenyl, thienyl, furyl, pyrrolyl , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, 1,3,4-oxadiazolyl,
    1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl.


    The term "fluorine source" refers to a chemical compound capable of releasing fluoride ions (F-). Examples include, but are not limited to, tetrabutylammonium fluoride (TBAF), tetraphenylphosphonium fluoride (TPPF), CsF, RbF, KF, NaF, LiF, BaF2, SrF2, CaF2, and
    5 MgF2.
    When in the definitions used throughout the present description for cyclic groups the specified examples refer to a ring radical in general terms, for example pyridyl, thienyl or indolyl, all the positions of
    10 possible union. Thus, for example, in the definitions of Cy1 to Cy4, which do not include any limitation regarding the binding position, the term pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; and thienyl includes 2-thienyl and 3-thienyl.
    The expression "optionally substituted by one or more"; means the possibility of a
    15 group being substituted by one or more, preferably by 1, 2, 3 or 4 substituents, more preferably by 1, 2 or 3 substituents and even more preferably by 1 or 2 substituents, provided that said group has sufficient available positions available of being replaced. If present, said substituents may be the same or different and may be located over any available position.
    20 When two or more groups with the same numbering appear in a definition of a substituent (for example -NR4R4, -NR8R8, etc.), this does not mean that they have to be identical. Each of them is independently selected from the list of possible meanings given for that group, and therefore they can be the same or
    25 different
    In another embodiment the invention relates to the process described above, wherein the fluorine source is selected from tetrabutylammonium fluoride (TBAF), tetraphenylphosphonium fluoride (TPPF), CsF, RbF, KF, NaF, LiF, BaF2, SrF2, CaF2, and MgF2, and
    30 preferably where the fluorine source is selected from tetrabutylammonium fluoride (TBAF) and KF.
    In another embodiment, the invention relates to the process described above, where each R1 independently represents hydrogen, halogen, C1-C20 alkyl,
    -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.


    In another embodiment, the invention relates to the process described above, wherein each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5.
    In another embodiment, the invention relates to the process described above, where each R2 independently represents Cy2 optionally substituted by one or more R7.
    In another embodiment, the invention relates to the process described above, where each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl it is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    In another embodiment, the invention relates to the process described above, where each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20 alkyl is optionally substituted by one or more R10 and where Cy4 is optionally substituted by one or more R11.
    In another embodiment, the invention relates to the process described above, wherein each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10.
    In another embodiment, the invention relates to the process described above,
    Where two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a heteroatom selected from N, O and S, and which may be optionally substituted by one or two R11.
    In another embodiment, the invention relates to the method described above, where each R6 independently represents R8.
    In another embodiment, the invention relates to the process described above, where each R7 independently represents C1-C40 alkyl optionally
    35 replaced by one or more R9.


    In another embodiment the invention relates to the process described above where each R8 independently represents C1-C6 alkyl optionally substituted by one or more -OH, -OC1-C4 alkyl and where C1-C4 alkyl is optionally substituted by one or more -OH.
    In another embodiment the invention relates to the process described above where each R9 independently represents -OR8 or Cy3, where Cy3 is optionally substituted by one or more C1-C6 alkyl.
    In another embodiment the invention relates to the process described above where each R10 independently represents -OR8 or Cy3, where Cy3 is optionally substituted by one or more C1-C6 alkyl.
    In another embodiment, the invention relates to the method described above, where each R11 independently represents R8.
    In another embodiment the invention relates to the process described above, where each Cy1 independently represents phenyl.
    In another embodiment the invention relates to the process described above, where each Cy1 independently represents a 5 or 6 membered aromatic heterocycle containing 1 or 2 heteroatoms selected from N, O and S, and where Cy1 can be attached to the rest of the molecule through any available C or N atom.
    In another embodiment the invention relates to the method described above, where each Cy1 independently represents:
    ;
    ;
    or
    .
    In another embodiment the invention relates to the process described above, where each Cy2 independently represents phenyl.


    In another embodiment the invention relates to the process described above, where each Cy2 independently represents a saturated, monocyclic ring of 3 to 7 carbocyclic members.
    In another embodiment the invention relates to the procedure described above,where each Cy2 independently represents a saturated, monocyclic ring of 3to 7 heterocyclic members, where Cy2 can be attached to the rest of the molecule athrough any available C or N atom, where Cy2 contains 1 to 3heteroatoms selected from N, O and S, and where one or more C or S atoms of Cy2
    10 may optionally be oxidized forming groups CO, SO or SO2.
    In another embodiment the invention relates to the process described above, where each Cy2 independently represents a saturated, monocyclic ring of 3 to 7 heterocyclic members, where Cy2 can be attached to the rest of the molecule a
    15 through any available C or N atom, and where Cy2 contains 1 to 3 heteroatoms selected from N, O and S.
    In another embodiment the invention relates to the process described above, where each Cy3 independently represents phenyl.
    In another embodiment, the invention relates to the process described above, where each Cy3 independently represents a 5 or 6 membered aromatic heterocycle containing 1 or 2 heteroatoms selected from N, O and S, and where Cy3 can be attached to the rest of the molecule through any atom of C or N
    25 available.
    In another embodiment the invention relates to the process described above, where each Cy4 independently represents a saturated heterocyclic ring, of 3 to 7 members, optionally containing 1 to 3 heteroatoms selected from
    30 N, O and S, where Cy4 is attached to the rest of the molecule through any available C or N atom, and where one or more C or S atoms of Cy4 can be optionally oxidized forming CO, SO or SO2 groups .
    In another embodiment the invention relates to the process described above,
    Where each Cy4 independently represents a saturated heterocyclic ring, 3 to 7 members, optionally containing 1 to 3 heteroatoms selected from


    N, O and S, and where Cy4 is attached to the rest of the molecule through any available C or N atom.
    In another embodiment the invention relates to the process described above, where each Cy4 independently represents phenyl.
    In another embodiment the invention relates to the process described above, where each R12 independently represents hydrogen, halogen, -OR4, -SR4, -SeR4, -NR4R4 or -PR4R4.
    In another embodiment, the invention relates to the process described above, wherein the compound of formula I is selected from a compound of formula Ia:
    fifteen where R1 and R3 have the meaning described for a compound of formula I.
    twenty In another embodiment, the invention relates to the process described above, wherein the compound of formula I is selected from a compound of formula Ib:


    Ib where R1 and R3 have the meaning described for a compound of formula I.
    In another embodiment, the invention relates to the process described above, wherein the compound of formula I is selected from a compound of formula Ic:
    Ic where R1 and R3 have the meaning described for a compound of formula I.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6; Y


    each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5.
    In another embodiment the invention relates to the process described above,
    5 where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R2 independently represents Cy2 optionally substituted by one or more
    10 R7.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    In another embodiment the invention relates to the process described above, where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally
    25 substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20 alkyl is optionally substituted by one or more R10 and where Cy4 is optionally substituted by one or more R11.
    In another embodiment the invention relates to the process described above, wherein: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl it is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; Y
    Each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10.


    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    5 -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a heteroatom selected from N, O and S, and which may be optionally substituted by one or two R11.
    In another embodiment the invention relates to the process described above, where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally
    15 substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R6 independently represents R8.
    In another embodiment the invention relates to the process described above, where:
    Each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each Cy1 independently represents phenyl.
    In another embodiment the invention relates to the process described above, where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl it is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; Y
    Each Cy1 independently represents a 5 or 6-membered aromatic heterocycle containing 1 or 2 heteroatoms selected from N, O and S, and where Cy1 can be attached to the rest of the molecule through any available C or N atom.
    In another embodiment the invention relates to the process described above, wherein:


    each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each Cy1 independently represents:
    ;
    ;
    or
    .
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7; Yeach R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7;each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6; Yeach R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20alkyl is optionally substituted by one or more R10 and where Cy4 isoptionally substituted by one or more R11.


    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionally
    5 substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5, preferably each R2 independently represents Cy2 optionally substituted by one or more R7; each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    10 -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10.
    In another embodiment the invention relates to the process described above, where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl it is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6;
    Each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5, preferably each R2 independently represents Cy2 optionally substituted by one or more R7; each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally
    25 substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10; and two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a selected heteroatom
    30 of N, O and S, and which may be optionally substituted by one or two R11.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6;


    each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7;each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20alkyl is optionally substituted by one or more R10 and where Cy4 isoptionally substituted by one or more R11; Yeach R6 independently represents R8.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7;each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R4 independently represents C1-C20 alkyl optionally substituted byone or more R10; Yeach R6 independently represents R8.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7;


    each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R4 independently represents C1-C20 alkyl optionally substituted by
    5 one or more R10; two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a heteroatom selected from N, O and S, and which may be optionally substituted by one or two R11; and each R6 independently represents R8.
    In another embodiment the invention relates to the process described above, where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally
    15 substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5, preferably each R2 independently represents Cy2 optionally substituted by one or more R7; each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20 alkyl is optionally substituted by one or more R10 and where Cy4 is optionally substituted by one or more R11;
    25 each R6 independently represents R8; and each Cy1 independently represents phenyl.
    In another embodiment the invention relates to the process described above, where:
    Each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5, preferably each R2 independently represents Cy2
    35 optionally substituted by one or more R7;


    each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R4 independently represents C1-C20 alkyl optionally substituted by
    5 one or more R10;each R6 independently represents R8; YEach Cy1 independently represents phenyl.
    In another embodiment the invention relates to the process described above,
    10 where: each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl optionally substituted by
    One or more R5, preferably each R2 independently represents Cy2 optionally substituted by one or more R7; each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6;
    20 each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10; two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a heteroatom selected from N, O and S, and which may be optionally substituted by one or two R11;
    25 each R6 independently represents R8; and each Cy1 independently represents phenyl.
    In another embodiment the invention relates to the process described above, where:
    Each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5, preferably each R2 independently represents Cy2
    35 optionally substituted by one or more R7;


    each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20alkyl is optionally substituted by one or more R10 and where Cy4 isoptionally substituted by one or more R11;each R6 independently represents R8; Yeach Cy1 independently represents a 5- or 6-membered aromatic heterocyclecontaining 1 or 2 heteroatoms selected from N, O and S, and where Cy1 can bebound to the rest of the molecule through any available C or N atom.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7;each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;each R4 independently represents C1-C20 alkyl optionally substituted byone or more R10;each R6 independently represents R8; Yeach Cy1 independently represents a 5- or 6-membered aromatic heterocyclecontaining 1 or 2 heteroatoms selected from N, O and S, and where Cy1 can bebound to the rest of the molecule through any available C or N atom.
    In another embodiment the invention relates to the process described above,where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6;


    each R2 independently represents C1-C40 alkyl optionally substituted byone or more R5, preferably each R2 independently represents Cy2optionally substituted by one or more R7;each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    5 -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10; two R4 groups can be joined to form a heterocycle of 5 to 7 with the N atom
    10 saturated members which may additionally contain a heteroatom selected from N, O and S, and which may be optionally substituted by one or two R11; each R6 independently represents R8; and each Cy1 independently represents a 5 or 6 member aromatic heterocycle containing 1 or 2 heteroatoms selected from N, O and S, and where Cy1 may be
    15 bound to the rest of the molecule through any available C or N atom.
    In another embodiment, the invention relates to the process described above, wherein the compound of formula I is selected from a compound of formula Ia:


    where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,-SR4, -SeR4, -NR4R4, –PR4R4 or Cy1, where C1-C20 alkyl is optionallysubstituted by one or more R5 and Cy1 is optionally substituted by one or more R6; Y
    5 each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    In another embodiment, the invention relates to the process described above, wherein the compound of formula I is selected from a compound of formula Ib:
    Ib
    where:
    Each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally
    20 substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    In another embodiment, the invention relates to the process described above, wherein the compound of formula I is selected from a compound of formula Ic:


    Ic
    where:each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4,
    5 -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; and each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, where C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    In another embodiment the invention relates to the process described above, wherein the compound of formula I is selected from the list of compounds described in examples 1 to 56.
    The compounds of the present invention contain one or more basic nitrogen and could therefore form salts with acids, both organic and inorganic. Examples of such salts include: salts with inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, perchloric acid, sulfuric acid or phosphoric acid; and salts with organic acids, such as methanesulfonic acid,
    20 trifluoromethanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, ptoluenesulfonic acid, fumaric acid, oxalic acid, acetic acid, maleic acid, ascorbic acid, citric acid, lactic acid, tartaric acid, malonic acid, glycolic acid, succinic acid and propionic acid, between others. Some compounds of the present invention may contain one or more acidic protons and therefore may form
    25 also salts with bases. Examples of such salts include: salts with cations


    inorganic such as sodium, potassium, calcium, magnesium, lithium, aluminum, zinc, etc .; and salts formed with pharmaceutically acceptable amines such as ammonia, alkylamines, hydroxyalkylamines, lysine, arginine, N-methylglucamine, procaine and the like.
    5 There is no limitation on the type of salt that can be used, provided thatwhen used for therapeutic purposes are pharmaceutically acceptable. Bemeans pharmaceutically acceptable salts those salts that, at the discretionmedical, are suitable for use in contact with the tissues of humans orother mammals without causing undue toxicity, irritation, allergic response or
    10 similar. Pharmaceutically acceptable salts are widely known to any person skilled in the art.
    The salts of a compound of formula I can be obtained during the final isolation and purification of the compounds of the invention or they can be prepared by
    Treatment of a compound of formula I with a sufficient amount of the desired acid or base to give the salt in a conventional manner. The salts of the compounds of formula I can in turn be transformed into other salts of compounds of formula I by ion exchange by means of an ion exchange resin.
    The compounds of formula I and their salts may differ in certain physical properties, but are equivalent for the purposes of the invention. All salts of the compounds of formula I are included within the scope of the invention.
    The compounds of the present invention can form complexes with solvents in which they are reacted or from which they are precipitated or crystallized. These complexes are known as solvates. As used herein, the term "solvate" refers to a complex of variable stoichiometry formed by a solute (a compound of formula I or a salt thereof) and a solvent. Examples of solvents include
    30 pharmaceutically acceptable solvents such as water, ethanol and the like. A complex with water is known as hydrate. Solvates of the compounds of the invention (or their salts), including hydrates, are included within the scope of the invention.
    The compounds of formula I can exist in different physical forms, that is, in amorphous form and crystalline forms. Also, the compounds of the present invention


    They may have the ability to crystallize in more than one way, a characteristic known as polymorphism. Polymorphs can be distinguished by several physical properties well known to those skilled in the art such as their x-ray diffractograms, melting points or solubility. All shapes
    The physical compounds of the compounds of formula I, including all their polymorphic forms ("polymorphs"), are included within the scope of the present invention.
    Some compounds of the present invention could exist in the form of several diastereoisomers and / or several optical isomers. The diastereoisomers can be separated by conventional techniques such as chromatography or fractional crystallization. Optical isomers can be resolved by using conventional optical resolution techniques, to give optically pure isomers. This resolution can be made on synthesis intermediates that are chiral or on products of formula I. Optically pure isomers can also be
    15 obtained individually using enantiospecific synthesis. The present invention covers both the individual isomers and their mixtures (for example racemic mixtures or mixtures of diastereoisomers), whether they are obtained by synthesis or by physically mixing them.
    As mentioned above, the method of the present invention allows substituents (R3) to be introduced in the bay positions of a POI at a stage in which a source of fluoride and an alcohol, thiol, selenol, amine or phosphine is involved.
    As will be apparent to one skilled in the art, the precise method used for the
    The preparation of a given compound may vary depending on its chemical structure. Also, in some of the procedures detailed below, it may be necessary or convenient to protect reactive or labile groups by conventional protecting groups. Both the nature of these protecting groups and the procedures for their introduction and elimination are well known and form
    30 part of the state of the art (see for example Greene T.W. and Wuts P.G.M, "Protective Groups in Organic Synthesis", John Wiley & Sons, 4th edition, 2006). Whenever a protective group is present, a subsequent deprotection stage will be necessary, which is carried out under the usual conditions in organic synthesis, such as those described in the reference mentioned above.


    Also, some compounds of the present invention can be obtained from other compounds of formula I by transformation reactions of suitable functional groups, in one or more stages, using reactions widely known in organic chemistry under the usual experimental conditions. These
    5 interconversions can be carried out independently on R1, R2 and R3 einclude:
    the replacement of a primary or secondary amine by treatment with an alkylating agent under standard conditions, or by reductive amination, that is, by treatment with an aldehyde or ketone in the presence of a reducing agent such as sodium cyanoborohydride or sodium triacetoxyborohydride;
    the transformation of an amine into a sulfonamide by reaction with a sulfonyl halide, such as sulfonyl chloride, optionally in the presence of amounts
    Catalysts of a base such as 4-dimethylaminopyridine, in a suitable solvent such as dioxane, chloroform, dichloromethane or pyridine, optionally in the presence of a base such as triethylamine or pyridine;
    the transformation of an amine into an amide under standard conditions;
    20 the alkylation of an amide by treatment with an alkylating agent under basic conditions;
    the conversion of an alcohol into an ether or ester under standard conditions; 25 the alkylation of a thiol to obtain a thioether, under standard conditions;
    partial or total oxidation of an alcohol to obtain ketones, aldehydes or carboxylic acids under standard oxidation conditions;
    30 the reduction of an aldehyde or ketone to alcohol, by treatment with a reducing agent such as sodium borohydride;
    the reduction of a carboxylic acid or a derivative of carboxylic acid to alcohol by treatment with a reducing agent such as diisobutylaluminum hydride or LiAlH4;


    the reduction of an amide to amine by treatment with a reducing agent such as LiAlH4;
    the oxidation of a thioether to sulfoxide or sulfone under standard conditions;
    5the transformation of an alcohol into a halogen by treatment with SOCl2, PBr3,tetrabutylammonium bromide in the presence of P2O5, or PI3;
    the transformation of a halogen atom into an amine by reaction with a
    10 amine, optionally in the presence of a suitable solvent, and preferably heating; Y
    the transformation of a primary amide into a -CN group or vice versa, of a -CN group into an amide by standard conditions.
    Similarly, any of the aromatic rings of the compounds of the present invention may undergo aromatic electrophilic substitution or aromatic nucleophilic substitution reactions, widely described in the literature.
    The compounds of formula II and III may be commercial or prepared by methods widely described in the literature from commercial products or by the interconversion reactions of functional groups described above for a compound of formula I, and may be conveniently protected.
    Throughout the description and the claims the word quot; comprehequot; and its variants are not intended to exclude other technical characteristics, additives, components or steps. For those skilled in the art, other objects, advantages and features of the invention will be derived partly from the description and partly from the practice of the invention. The following examples are provided by way of illustration, and are not
    30 is intended to be limiting of the present invention.
    EXAMPLES
    The invention is illustrated below by tests carried out by the inventors, which demonstrates the effectiveness of the product of the invention.


    ALCOXI-PDI
    Method 1: Synthesis of 1-alkoxyperylene-3,4: 9,10-tetracarboxyidiimide
    0.1 mmol of perylene-3,4: 9,10 are dissolved in a heart-shaped flask
    5 tetracarboxyidiimide in 0.3 mL of dry THF. Then 0.4 mmol of the corresponding alcohol and 0.24 mmol of TBAF (1M solution in THF) are added. It is heated at 70 ° C under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with gel
    10 of silica and toluene as eluent, unless otherwise specified.
    Method 2: Synthesis of 1,6 (7) -dialkoxyperylene-3,4: 9,10-tetracarboxyidiimide
    In a round bottom flask, 0.1 mmol of perylene-3.4: 9.10 tetracarboxyidiimide are dissolved in 2 mL of dry THF. 1.2 mmol of the
    15 corresponding alcohol and 0.48 mmol of TBAF (1M solution in THF). It is heated under reflux of THF under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent, unless otherwise specified.
    Method 3: Synthesis of 1-alkoxyperylene-3,4: 9,10-tetracarboxyidiimide
    In a heart-shaped flask, 0.1 mmol of 1-bromoperylene3.4: 9,10-tetracarboxyidiimide are dissolved in 0.3 mL of dry THF. Then 0.4 mmol of the corresponding alcohol and 0.24 mmol of TBAF (1M solution in THF) are added. Be
    25 heats at 70 ° C under argon for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent.
    Method 4: Synthesis of 1,6 (7) -dialkoxyperylene-3,4: 9,10-tetracarboxydiimide. 0.1 mmol of 1-butoxyperylene-3,4: 9,10 tetracarboxyidiimide are dissolved in 2 mL of dry THF in a round bottom flask. Then 1.2 mmol of the corresponding alcohol and 0.48 mmol of TBAF (1M solution in THF) are added. It is heated under reflux of THF under an argon atmosphere for 24 hours. The crude dissolves in
    35 CH2Cl2 and wash with water. The organic phase is dried with Na2SO4, filtered and removed.


    the solvent under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent.
    Method 5: Synthesis of N, N’-di- (1’-hexylheptyl) -2,5,8,11-tetrabutoxyperylene
    5 3,4: 9,10-tetracarboxyidiimide, N, N'-di- (1'-hexylheptyl) -2-bromo-5,8,11-tributyloxyperylene-3,4: 9,10-tetracarboxyidiimide and N, N'- di- (1'-hexylheptyl) -2,5-dibromo-8,11-dibutoxyperylene-3,4: 9,10-tetracarboxyidiimide
    0.05 mmol of 2.5.8.11 are dissolved in a heart-shaped flask
    Tetrabromoperylene-3,4: 9,10-tetracarboxyidiimide in 0.5 mL of dry THF. Then 0.5 mmol of the corresponding alcohol, 0.15 mmol of CsF and 0.03 mmol of 18-crown-6 are added. It is heated at 70 ° C under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified
    15 by column chromatography with silica gel and CH2Cl2: Hexane 1: 1 as eluent.
    Example 1: N, N’-di- (1’-hexylheptyl) -1-methoxyperylene-3,4: 9,10-tetracarboxy diimide
    (one)
    Compound 1 is prepared following method 1. Yield: 33%. It is purified by column chromatography with silica gel and chloroform: hexane 4: 1 as
    eluent 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.24 (broad s, 32H), 1.87 (m, 4H), 2.25 (m, 4H), 4.34 (s, 3H), 5.20 (m, 2H), 8.57 (m, 6H), 9.49 (d, 1H); 13C-NMR (CDCl3) G 14.02,


    22.57, 26.94, 29.21, 29.22, 31.76, 32.38, 54.61, 56.84, 120.74, 121.46, 121.87, 123.01, 123, 41, 124.46, 126.96, 128.39, 128.53, 129.20, 133.92, 134.30, 134.48, 158.29, 163.54, 164.54; MALDI-TOF MS m / z. > M + H + @ theoretical C51H64N2O5 785.48, found 785.46; IR (KBr): 2855, 1695, 1658, 1597, 1462, 1409, 1327, 1262, 1094, 804, 747 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 514 (5.7), 552 (5.9).
    Example 2: N, N’-di- (1’-hexylheptyl) -1.6 (7) -dimethoxyperylene-3.4: 9,10 tetracarboxidiimide (2)
    Compound 2 is obtained following method 2. Yield: 6% (50% isomer 1.6; 50% isomer 1.7 approx.). It is purified by column chromatography with silica gel and chloroform: hexane 4: 1 as eluent. 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.23 (broad s, 32H), 1.87 (m, 4H), 2.28 (m, 4H), 4.31 (d, 6H), 5.21 (m, 2H), 8.64 (m, 4H),
    9.46 (is, omero 1.6) (d, 1H) 9.54 (isomer 1.7) (d, 1H); 13C-NMR (CDCl3) G 14.03, 22.58, 26.94, 29.21, 29.22, 29.24, 31.75, 31.76, 31.77, 32.42, 54.46 , 54.96, 56.85, 119.38, 120.86, 121.56, 121.97, 123.51, 124.54, 127.07, 127.36, 127.92, 128.50, 128 , 61, 128.68, 129.27, 130.79, 132.58, 133.75, 134.14, 134.41, 157.33, 158.45, 163.88, 164.77; MALDI-TOF MS m / z. > M + H + @ theoretical C51H64N2O5 815.49,
    20 experimental 815.52; IR (KBr): 2920, 2850, 1695, 1654, 1590, 1456, 1397, 1327, 808, 150 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 523 (4.6), 556 (4.7).
    Example 3: N, N’-di- (1’-hexylheptyl) -1-ethoxyperylene-3,4: 9,10-tetracarboxyidiimide (3)


    Compound 3 is obtained following method 1. Yield: 36%. 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.24 (broad s, 32H), 1.73 (t, 3H), 1.89 (m, 4H), 2.27 (m, 4H), 5.54 (m, 2H), 5.20 (m, 2H), 8.48 (m, 6H), 9.50 (d, 1H); 13C-NMR (CDCl3) G 14.01, 15.01, 22.56, 26.94, 26.95, 29.19, 29.22, 29.65, 31.74, 31.75, 32.35 , 54.56, 54.80, 66.11, 70.55, 120.31, 121.63, 123.18, 124.20, 126.79, 128.20, 129.06, 133.64, 134 , 29, 157.56, 163.54, 164.52; MALDI-TOF MS m / z. > M + H + @ theoretical C52H66N2O6 799.50, experimental 799.53; IR (KBr): 2855, 1770, 1662, 1585, 1458, 1323, 1258, 804, 747;
    10 UV Vis (CH2Cl2), Omax / nm (log H): 518 (4.7), 553 (4.8).
    Example 4: N, N’-di- (1’-hexylheptyl) -1.6 (7) -diethoxyperylene-3.4: 9.10
    tetracarboxyidiimide (4)


    Compound 4 is obtained following method 2. Yield: 5% (60% isomer 1.6; 40% isomer 1.7 approx.). 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.23 (broad s, 32H), 1.74 (t, 6H), 1.86 (m, 4H), 2.27 (m, 4H), 4.57 (c, 4H), 5.20 (m, 2H), 8.39-8.67 (m, 4H), 9.57 5 (1.6 isomer) (d, 1H), 9.64 isomer 1.7 (d, 1 H); 13C-NMR (CDCl3) G 14.02, 15.07, 22.57, 26.91, 29.22, 29.24, 31.75, 31.76, 32.40, 54.48, 66.13 , 119.21, 123.86, 127.21, 128.56, 128.64, 129.31, 130.78, 133.91, 133.98, 134 30, 135.87, 136.00, 144, 10, 144.68, 150.12, 156.68, 157.68, 163.61, 164.68; MALDI-TOF MS m / z. > M + H + @ theoretical C54H70N2O6 843.53, experimental 843.54; IR (KBr): 2920, 2838, 1736, 1706, 1660,
    10 1590, 1333, 796, 750 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 531 (4.5), 568 (4.6).
    Example 5: N, N’-di- (1’-hexylheptyl) -1-butoxyperylene-3,4: 9,10-tetracarboxyidiimide
    (5)


    Compound 5 is obtained following method 3. Yield: 88%. 1H-NMR (CDCl3) G 0.82 (t, 12H), 1.10 (t, 3H), 1.25 (broad s, 32H), 1.68 (m, 2H), 1.87 (m, 4H), 2.07 (m, 2H), 2.26 (m, 4H), 4.53 (t, 2H), 5.20 (m, 2H), 8.60 (m, 6H), 9, 60 (d, 1 H); 13C5 NMR (CDCl3) G 13.86, 14.02, 19.56, 22.57, 26.94, 29.20, 29.23, 29.67, 31.37, 31.75, 31.76, 32.36, 54.57, 70.36, 120.47, 121.73, 123.31, 124.25, 126.90, 128.25, 128.30, 129.16, 133.76, 134, 42, 157.82, 163.67, 164.53; MALDI-TOF MS m / z. > M + @ theoretical C54H70N2O5 826.52, experimental 826.51; IR (KBr): 2955, 2926, 2838, 1701, 1654, 1590, 1456, 1333, 1251, 814, 755 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 518 (4.8),
    10 554 (4.9).
    Alternatively, compound 5 is obtained following method 1. Yield: 75%.
    Example 6: N, N’-di- (1’-hexylheptyl) -1.6 (7) -dutoxyperylene-3.4: 9,1015 tetracarboxyidiimide (6)


    Compound 6 is obtained following method 3. Yield: 4%. 1H-NMR (CDCl3) G 0.82 (t, 12H), 1.08 (t, 6H), 1.25 (broad s, 32H), 1.68 (m, 4H), 1.87 (m, 4H), 2.07 (m, 4H), 2.27 (m, 4H), 4.50 (t, 4H), 5.15 (m, 2H), 8.50 (m, 4H), 9, 56 (1.6 isomer) (d, 1H), 9.63 (1.7 isomer) (d, 1H); 13C-NMR (CDCl3) G 13.85, 14.02, 19.57, 22.57, 22.58, 26.90, 26.92, 29.20, 29.22, 29.25, 29.68 , 31.42, 31, 74, 31.75, 31.77, 32.41, 54.43, 54.88, 70.31, 119.06, 120.70, 123.84, 127.17, 127 , 95, 128.54, 128.70, 129.27, 129.81, 130.76, 134.31, 156.86, 158.02, 163.81, 164.74; MALDI-TOF MS m / z:> M + @ theoretical C58H78N2O6 898.58, experimental 898.57; IR (KBr): 2955, 2920, 2844, 1695, 1649, 10 1596, 1467, 1327, 814, 744 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 530 (4.2), 569 (4.3).
    Alternatively, compound 6 can be obtained following method 2. Yield: 50% (72% isomer 1.6; 28% isomer 1.7 approx.).
    Example 7: N, N’-di- (1’-hexylheptyl) -1-s-butoxyperylene-3,4: 9,10-tetracarboxyidiimide
    (7)


    Compound 7 is obtained following method 1. Yield: 35%; 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.12 (t, 3H), 1.25 (broad s, 35H), 1.87 (m, 4H), 2.10 (m, 2H), 2.26 (m, 4H), 4.98 (m, 1H), 5.20 (m, 2H), 8.49-8.66 (m, 6H), 9.72 (d, 1H ); 13C-NMR
    5 (CDCl3) G 9.83, 14.02, 19.83, 22.57, 26.57, 26.92, 29.20, 29.23, 29.63, 29.68, 31.74, 31 , 75, 54.57, 78.78, 121.86, 123.44, 124.37, 127.12, 128.36, 128.68, 129.27, 133.91, 134.65, 157.75 , 163.12, 164.85; MALDI-TOF MS m / z. > M + @ theoretical C54H70N2O5 826.52, experimental 826.53; IR (KBr): 2920, 2850, 1695, 1660, 1584, 1403, 1327, 1251 cm1; UV Vis (CH2Cl2), Omax / nm (log H) : 520 (4.8), 554 (4.9).
    Example 8: N, N’-di- (1’-hexylheptyl) -1.6 (7) -di-s-butoxyperylene-3.4: 9.10
    tetracarboxyidiimide (8)


    Compound 8 is obtained following method 2. Yield: 6% (58% isomer 1.6; 42% isomer 1.7 approx.). 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.09 (t, 6H), 1.25 (broad s, 38H), 1.88 (m, 4H), 2.21 (m, 4H), 2.27 (m, 4H), 4.94 (m, 2H), 5.22 (m, 2H), 8.39-8.76 (m, 4H), 9.60 (isomer 1, 6) (d, 1H), 9.67 (1.7 isomer) (d, 1H); 13C-NMR (CDCl3) G 5 9.83, 14.02, 14.11, 19.69, 22.53, 22.68, 26.90, 28.21, 29.20, 29.36, 29, 69, 30.91, 31.23, 31.43, 31.76, 31.92, 32.43, 33.14, 33.21, 3.80, 33.82, 37.09, 38.14, 39.22, 54.84, 59.57, 114.05, 127.25, 128.08, 128.74, 129.0, 129.28, 129.31, 129.54, 129.83, 130, 15, 130.19, 139.26, 157.43, 163.24, 164.76; MALDI-TOF MS m / z. > M + @ theoretical C58H78N2O6 898.58, experimental 898.55; IR (KBr): 2932, 2844, 1695, 1666, 1601,
    10 1467, 1321, 814 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 525 (4.0), 564 (4.0).
    Example 9: N, N’-di- (1’-hexylheptyl) -1-i-butoxyperylene-3,4: 9,10-tetracarboxyidiimide
    (9)
    Compound 9 is obtained following method 1. Yield: 46%. 1H-NMR (CDCl3) G 0.82 (t, 12H), 1.25 (broad s, 38H), 1.89 (m, 4H), 2.27 (m, 4H), 2.44 (m, 2H), 4.30 (d, 2H), 5.20 (m, 2H), 8.59 (m, 6H), 9.63 (d, 1H); 13C-NMR (CDCl3) G 14.01, 19.54, 22.57, 22.58, 26.93, 28.56, 29.20, 29.23, 29.66, 31.75, 32.36 , 54.58, 120.56,
    20 121.75, 123.34, 124.26, 126.90, 128.29, 128.32, 129.17, 133.78, 134.43, 157.90, 163.80, 164.85; MALDI-TOF MS m / z. > M + @ theoretical C54H70N2O5 826.52, experimental 826.51; IR (KBr): 2949, 2926, 2850, 1695, 1654, 1584, 1456, 1333, 1263, 808, 744 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 517 (4.4), 554 (4.6).


    Example 10: N, N’-di- (1’-hexylheptyl) -1.6 (7) -di-i-butoxyperylene-3,4: 9,10 tetracarboxidiimide (10)
    Compound 10 is obtained following method 2. Yield: 18% (75% isomer
    5 1.6; 25% isomer 1.7 approx.). 1H-NMR (CDCl3) G 0.84 (t, 12H), 1.25 (broad s, 44H), 1.8 (m, 4H), 2.29 (m, 4H), 2.41 (m, 2H), 4.27 (d, 4H), 5.20 (m, 2H), 8.50 (m, 4H), 9.57 (1.6 isomer) (d, 1H), 9.64 (isomer 1.7) (d, 1 H); 13C-NMR (CDCl3) G 14.03, 19.56, 22.57, 22.58, 26.88, 26.93, 28.61, 29.20, 29.23, 29.26, 29.68 , 31.75, 31.76, 32.42, 54.46, 54.89, 119.06, 120.80, 123.85, 127.29, 127.98, 128.74, 129.29, 130 , 79, 134.29,
    10 156.98, 158.14, 163.82, 164.91; MALDI-TOF MS m / z. > M + @ theoretical C58H78N2O6 898.58, experimental 898.54; IR (KBr): 2955, 2920, 2858, 1696, 1648, 1596, 1458, 1327, 802, 755 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 539 (4.5), 570 (4.6).
    Example 11: N, N’-di- (1’-hexylheptyl) -1-decanoxyperylene-3,4: 9,1015 tetracarboxyidiimide (11)


    Compound 11 is obtained by method 1. Yield: 60%. 1H-NMR (CDCl3) G 0.82 (t, 15H), 1.25 (broad s, 44H), 1.6 (m, 2H), 1.87 (m, 4H), 2.12 (m, 2H), 5.26 (m, 4H), 4.53 (t, 2H), 5.20 (m, 2H), 8.60 (m, 6H), 9.64 (d, 1H); 13C-NMR (CDCl3) G 14.02, 14.08, 22.57, 22.65, 26.30, 2693, 29.20 29.23, 29.28, 29.33, 29.55, 29, 56, 31.75, 31.75, 31.87, 32.37, 54.58, 70.69, 120.55, 121.80, 123.38, 124.31, 126.98, 128.33, 128.38, 129.21, 133.84, 134.51, 157.89, 163.54, 164.62; MALDI-TOF MS m / z. > M + @ theoretical C60H82N2O5 910.62, experimental 910.63; IR (KBr): 2926, 2844, 1701,
    10 1660, 1584, 1461, 1316, 1257, 855, 802, 744 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 518 (4.5), 554 (4.6).
    Example 12: N, N’-di- (1’-hexylheptyl) -1.6 (7) -didecanoxyperylene-3.4: 9,10 tetracarboxyidiimide (12)


    Compound 12 is obtained according to method 2. Yield: 20% (74% isomer 1.6; 26% isomer 1.7 approx.). The reaction time was 72h. 1 H-NMR (CDCl 3) G 0.82 5 (m, 18H), 1.25 (broad s, 56H), 1.6 (m, 4H), 1.87 (m, 4H), 2.08 (m , 4H), 2.27 (m, 4H), 4.49 (t, 4H), 5.20 (m, 2H), 8.39-8.67 (m, 4H), 9.57 (isomer 1 , 6) (d, 1H), 9.64 (1.7 isomer) (d, 1H); 13C-NMR (CDCl3) G 14.03, 14.09, 22.58, 22.66, 26.30, 26.93, 29.28, 29.55, 29.69, 31.75, 31.76 , 31.77, 31.87, 32.43, 37.10, 54.44, 54.90, 70.65, 119.10, 120.77, 123.88, 127.22, 128.01, 128 , 74, 130.82, 134.34, 156.91, 158.07, 163.69,
    10 164.88; MALDI-TOF MS m / z. > M + H + @ theoretical C70H102N2O6 1067.78, experimental 1067.81; IR (KBr): 2908, 2844, 1701, 1642, 1590, 1461, 1321 cm-1; UV Vis (CH2Cl2), Omax / nm (log H): 535 (4.6), 571 (4.7).
    Example 13: N, N’-di- (1’-hexylheptyl) -1-phenylmethoxyperylene-3,4: 9,1015 tetracarboxy diimide (13)


    Compound 13 is obtained following method 1. Yield: 18%. 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.25 (broad s, 32H), 1.88 (m, 4H), 2.27 (m, 4H), 5.18 (m, 2H), 5.59 (s, 2H) 8.62 (m, 6H), 9.58 (d, 1H); 13C-NMR (CDCl3) G 14.01, 22.56, 26.91, 29.19,
    5 29.21, 31.74, 32.37, 54.58, 70.56, 72.49, 121.12, 121.98, 123.52, 124.62, 127.04, 128.10, 128 , 52, 128.76, 128.98, 129.07, 129.22, 134.05, 134.30, 135.06, 157.41, 163.79, 164.66; MALDI-TOF MS m / z. > M + H + @ theoretical C57H68N2O5 861.52, experimental 861.53; IR (KBr): 2920, 2938, 1695, 1636, 1601, 1327, 1257, 802, 744 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 514 (4.5), 550 (4.7).
    10 Example 14: N, N’-di- (1’-hexylheptyl) -1-phenethoxyperylene-3,4: 9,10 tetracarboxyidiimide (14)


    Compound 14 is obtained following method 1. Yield: 44%. The reaction time for this compound was 72 hours. 1 H-NMR (CDCl 3) G 0.83 (t, 12H), 1.25 (broad s, 32H), 1.90 (m, 4H), 2.26 (m, 4H), 3.42 (t, 2H), 4.75 (m, 2H), 5.20 (m, 2H), 7.33-7.46 (m, 5H), 8.47 (m, 6H), 9.20 (d, 1 HOUR) ; 13C-NMR (CDCl3) G 14.02, 22.57, 26.93, 26.96, 29.20, 29.23, 29.67, 31.75, 31.76, 32.36, 32.39 , 35.82, 54.61, 54.88, 71.02, 120.70, 121.76, 122.87, 123.34, 124.36, 126.82, 127.13, 128.32, 128 , 67, 128.89, 129.10, 133.84, 134.11, 134.35, 137.42, 157.45, 163.80, 164.57; MALDI-TOF MS m / z. > M + @ theoretical C58H70N2O5 874.53, experimental 874.24; IR (KBr): 2955, 2932, 10 2850, 1695, 1648, 1590, 1421, 1327, 1263, 808, 744 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 517 (4.6), 552 (4.78).
    Example 15: N, N’-di- (1’-hexylheptyl) -1.6 (7) -difenethoxyperylene-3.4: 9,10 tetracarboxyidiimide (15)


    Compound 15 is obtained following method 2. Yield: 54% (72% isomer 1.6; 28% isomer 1.7 approx.); 1H-NMR (THF-d8) G 0.84 (t, 12H), 1.30 (broad s, 32H), 1.85 (m, 4H), 2.35 (m, 4H), 3.37 ( t, 4H), 4.73 (t, 4H), 5.22 (m, 2H), 7.25 (t, 2H), 7.39 (t, 5 4H), 7.51 (d, 4H) , 8.35 (m, 4H), 9.12 (1.6 isomer) (d, 1H), 9.20 (1.7 isomer) (d, 1H); 13C-NMR (CDCl3) G 14.02, 22.57, 22.59, 26.87, 26.92, 26.96, 29.19, 29.22, 29.26, 29.35, 29.69 , 31.74, 31.76, 31.78, 32.39, 32.42, 32.44, 35.85, 54.47, 54.89, 71.00, 71.06, 119.26, 123 , 86, 127.04, 127.06, 127.58, 127.82, 128.53, 128.85, 128.89, 130.76, 137.56, 156.47, 157.60; MALDI-TOF MS m / z:> M + @ theoretical C66H78N2O6: 994.58,
    10 experimental: 994.58; IR (KBr): 2955, 2914, 2850, 1695, 1642, 1590, 1467, 1231 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 534 (4.6), 570 (4.7). Example 16: N, N’-di- (1’-hexylheptyl) -1-butoxy-6 (7) -decanoxyperylene3,4: 9,10-tetracarboxyidiimide (16)


    Compound 16 is obtained following method 4. Yield: 23% (72% isomer 1.6; 28% isomer 1.7). 1 H-NMR (CDCl 3) G 0.83 (m, 18H), 1.29 (broad s, 42H), 1.45 (m, 4H), 1.63 (m, 4H), 1.86 (m, 4H), 2.08 (m, 2H), 2.28 (m, 4H), 4.49 (t, 4H), 5.20 (m, 2H), 5 8.55 (m, 4H), 9 , 56 (1.6 isomer) (d, 1H), 9.65 (1.7 isomer) (d, 1H); 13C-NMR (CDCl3) G 14.02, 14.08, 22.57, 22.65, 26.30, 26.90, 26.93, 29.20, 29.22, 29.25, 29.28 , 29.31, 29.36, 29.54, 31.75, 31.77, 31.87, 32.42, 54.43, 54.88, 70.63, 119.06, 120.72, 123 , 85, 127.19, 127.97, 128.56, 128.72, 129.29, 130.45, 130.78, 131.17, 134.32, 156.88, 158.04, 163.70 , 164.10, 164.64, 165.14; MALDI-TOF MS m / z. > M + @ theoretical C64H90N2O6
    10 982.68, experimental 981.54; IR (KBr): 2955, 2926, 2844, 1686, 1685, 1596, 1467, 1321, 855, 802, 744 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 536 (5.1), 570 (5.2).

    Example 17: N, N'-di- (1'-hexylheptyl) -1- {2 '[2' '- (2' '- hydroxyethoxy) ethoxy] ethoxy} perylene3,4: 9,10-tetracarboxyidiimide (17 )



    Compound 17 is obtained following method 1. Yield: 7% The reaction time for this compound was 72 hours. It is purified by column chromatography with silica gel and toluene: methanol 9: 1 as eluent. 1H-NMR (CDCl3) G 5 0.83 (t, 12H), 1.25 (broad s, 32H), 1.86 (m, 4H), 2.26 (m, 4H), 3.69 (m , 2H), 3.77 (m, 2H), 3.84 (m, 2H), 3.90 (m, 2H), 4.13 (m, 2H), 4.68 (m, 2H), 5 , 20 (m, 2H), 8.48 (m, 6H), 9.79 (d, 1H); 13C-NMR (CDCl3) G 14.03, 22.57, 26.91, 29.20, 29.21, 29.68, 31.74, 31.75, 32.38, 54.65, 31.74 , 68.45, 69.26, 69.54, 70.60, 70.65, 71.00, 71.08, 71.19, 72.44, 72.72, 121.24, 122.01, 123 , 56, 124.67, 127.11, 128.53, 129.14, 129.25, 134.12,
    10 134.49, 157.59, 163.73, 164.82; MALDI-TOF MS m / z. > M + @ theoretical C56H74N2O8 902.54, experimental 902.55; IR (KBr): 2955, 2926, 2844, 1736, 1683, 1596, 1666, 1461, 1333, 1129, 808, 744 cm1; UV Vis (CH2Cl2), Omax / nm (log H): 516 (4.6), 551 (4.75).

    Example 18: N, N’-di- (1’-hexylheptyl) -1- (2’-hydroxyethoxy) perylene-3,4: 9,1015 tetracarboxyidiimide (18)


    Compound 18 is obtained following method 1. Yield: 43%. The reaction time for this compound was 72 hours. It is purified by column chromatography with silica gel and toluene: methanol 9: 1 as eluent. 1 H-NMR (THF-d8) G 5 0.86 (t, 12H), 1.35 (broad s, 32H), 1.88 (m, 4H), 2.32 (m, 4H), 4.17 (t, 2H), 4.57 (t, 2H), 5.18 (m, 2H), 8.40 (m, 6H), 9.60 (d, 1H); 13C-NMR (CDCl3) G 14.02, 22.58, 26.97, 29.23, 31.76, 32.35, 47.17, 54.67, 61.25, 63.03, 69.32 , 70.53, 71.62, 121.78, 122.03, 123.29, 124.45, 126.76, 128.22, 128.47, 129.03, 129.80, 134.14, 134 , 22, 157.39; MALDI-TOF MS m / z:> M + @ theoretical C52H66N2O6: 814.49, experimental: 814.48; IR (KBr): 10 3451, 2955, 2926, 2850, 1695, 1648, 1578, 1339 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 512 (4.6), 547 (4.7).
    Example 19: N, N’-di- (1’-hexylheptyl) -1- (8’-hydroxyoctyloxy) perylene-3,4: 9,10 tetracarboxidiimide (19)



    Compound 19 can be prepared following method 1. Yield: 26%. 1H-NMR (THF-d8) G 0.86 (t, 12H), 1.42 (broad s, 42H), 1.88 (m, 4H), 2.16 (m, 2H), 2.33 ( m, 4H), 3.51 (t, 2H), 4.50 (t, 2H), 5.19 (m, 2H), 8.41 (m, 6H), 9.44 (d, 1H); 13C-NMR
    5 (CDCl3) G 22.57, 25.70, 26.24, 26.92, 29.20, 29.22, 29.25, 29.34, 31.75, 32.38, 32.71, 54 , 64, 62.90, 70.71, 120.63, 121.91, 123.52, 124.38, 127.06, 128.38, 128.46, 128.64, 129.26, 133.95 , 134.63, 157.96; MALDI-TOF MS m / z:> M + @ theoretical C58H78N2O6: 898.58, experimental: 998.61; IR (KBr): 3440, 2958, 2921, 2847, 1699, 1650, 1580, 1323 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 518 (4.8), 554 (4.9).
    10 Example 20: N, N’-di- (1’-hexylheptyl) -1.6 (7) -di- (8’-hydroxyoctyloxy) perylene-3.4: 9,10 tetracarboxyidiimide (20)



    Compound 20 is obtained following method 2. Yield: 48% (75% isomer 1.6; 25% isomer 1.7 approx.); 1H-NMR (THF-d8) G 0.85 (t, 12H), 1.40 (broad s, 52H), 1.86 (m, 4H), 2.12 (m, 4H), 2.35 ( m, 4H), 3.50 (t, 4H), 4.49 (t, 4H), 5.20 (m, 2H), 8,278.55 (m, 4H), 9.48 (1.6 isomer) (d, 1H), 9.56 (isomer 1.7) (d, 1H); 13C-NMR (CDCl3)
    5 G 14.03, 22.58, 25.68, 26.24, 26.91, 26.92, 29.20, 29.22, 29.24, 29.36, 29.68, 31.75, 31, 76, 32.40, 32.73, 54.54, 54.92, 62.91, 70.63, 72.23, 123.41, 123.82, 127.17, 127.93, 128.71, 130.73, 131.96, 134.39, 158.08; MALDI-TOF MS m / z:> M + @ theoretical C66H94N2O8: 1042.70, experimental: 1042.72; IR (KBr): 3444, 2917, 2855, 1699, 1650, 1585 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 539 (4.7), 569 (4.7).
    Example 21: N, N’-di- (1’-hexylheptyl) -2,5,8,11-tetrabutoxyperylene-3,4: 9,10 tetracarboxyidiimide (21)
    Compound 21 is obtained according to method 5. Yield: 8%. 1H-NMR (CDCl3) G 0.83 (t, 12H), 1.05 (t, 12H), 1.25 (br, 32H), 1.65 (m, 8H), 1.86 (m, 4H ), 2.04 (m, 8H), 2.23 (m, 4H), 4.44 (m, 8H), 5.19 (m, 2H), 7.99 (s, 4H). 13C-NMR (CDCl3) G 13.76, 13.96, 19.08, 22.48, 26.90, 29.20, 29.56, 31.24, 31.70, 32.22, 53.27 , 53.86, 70.37, 98.82, 109.73, 116.65, 133.87, 162.74. MALDI-TOF MS m / z:> M + H + @ theoretical
    20 C66H94N2O8 1043.70, experimental 1043.71. IR (KBr): 2973, 2920, 2844, 1689, 1648, 1590, 1351, 1257, 855 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 412 (4.2), 497 (4.5), 535 (4.6).


    Example 21a: N, N’-di- (1’-hexylheptyl) -2-bromo-5,8,11-tributoxyperylene-3,4: 9,10 tetracarboxyidiimide (21a)
    Compound 21a is obtained according to method 5. Yield: 28%. 1 H-NMR (CDCl3)
    5 G 0.83 (t, 12H), 1.06 (m, 9H), 1.24 (br, 32H), 1.65 (m, 6H), 1.86 (m, 4H), 2.04 (m, 6H), 2.22 (m, 4H), 4.45 (m, 6H), 5.19 (m, 2H), 7.95 (s, 1H), 8.00 (s, 1H) , 8.09 (s, 1 H), 8.52 (s, 1 H). 13C-NMR (CDCl3) G 13.86, 13.89, 14.05, 19.19, 19.21, 22.58, 22.61, 27.00, 27.03, 29.25, 29.33 , 31.31, 31.35, 31.38, 31.78, 31.82, 32.27, 32.33, 54.04, 70.40, 70.57, 110.00, 116.46, 120 , 63, 128.49, 132.08, 133.26, 133.36, 133.95, 134.06,
    10 162.65, 162.83, 162.87. MALDI-TOF MS m / z:> M + @ theoretical C62H85N2O7Br 1048.55, experimental 1048.72. IR (KBr): 2949, 2926, 2862, 2360, 1695, 1642, 1549, 1339, 1251, 1100, 796 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 403 (4.3), 496 (4.7), 535 (4.8).


    Example 21b: N, N’-di- (1’-hexylheptyl) -2,5-dibromo-8,11-dibutoxyperylene-3,4: 9,10 tetracarboxyidiimide (mixture of isomers) (21b)
    21b Compound 21b is obtained following method 5. Yield: 29%. 1 H-NMR
    5 (CDCl3) G 0.83 (t, 12H), 1.06 (m, 6H), 1.24 (br, 32H), 1.67 (m, 4H), 1.89 (m, 4H), 2.05 (m, 4H), 2.22 (m, 4H), 4.48 (q, 4H), 5.17 (m, 2H), 8.12 (d, 2H), 8.54 (d , 2H). 13C-NMR (CDCl3) G 12.86, 13.05, 18.17, 18.19, 21.58, 25.99, 28.24, 28.68, 30.32, 30.77, 31.25 , 69.57, 69.70, 110.93, 119.34, 119.45, 127.54, 128.13, 131.03, 131.59, 132.28, 133.28, 133.81, 161 , 63. MALDI-TOF MS m / z:> M + H + @ theoretical C58H76N2O6Br2 1055.40,
    10 experimental 1055.34. IR (KBr): 2973, 2920, 2844, 1689, 1648, 1590, 1351, 1257, 855 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 405 (4.1), 494 (4.5), 530 (4.6).
    Example 22: N, N’-di- (1’-hexylheptyl) -1-hydroxyperylene-3,4: 9,10-tetracarboxy diimide
    (22) fifteen


    Compound 22 is obtained following method 1. Yield: 40%. As reagent
    Water is used instead of alcohol. It is purified by column chromatography
    with silica gel and hexane: dioxane 4: 1 as eluent. 1 H-NMR (THF-d8) G 0.85 (t,
    5 12H), 1.27-1.29 (m, 32H), 1.88 (m, 4H), 2.32 (m, 4H), 5.21 (m, 2H), 8.08-8, 49 (m, 6H),
    9.48 (d, 1 H), 11.03 (s, 1 H); 13C-NMR (CDCl3) G 13.94, 14.03, 22.5, 22.60, 26.96,
    27.025, 29.18, 29.25, 31.67, 31.80, 32.41, 70.46, 118.70, 121.59, 122.89, 122.92,
    122.95, 124.15, 124.24, 126.49, 128.35, 128.98, 129.03, 132.71, 134.27, 134.32,
    140.52, 156.05, 219.99; MALDI-TOF MS m / z:> M-H @ theoretical C50H61N2O5: 769.45, experimental 10: 769.44; IR (KBr): 3552, 2949, 2929, 2847, 1736, 1695, 1658, 1580,
    1331 cm -1; UV Vis (CH2Cl2), Omax / nm (log H): 504 (4.6), 541 (4.8).
    RENT-POI
    Method 1: Synthesis of 1-alkyl (aryl) aminoperylene-3,4: 9,10-tetracarboxyidiimide N, N'-disubstituted
    0.2 mmol of perylene-3.4: 9.10 are added to a 5 mL heart flask
    N, N'-disubstituted tetracarboxyidiimide, 0.48 mL tetrabutylammonium fluoride
    (1M solution in THF, 0.48 mmol), 0.48 mmol of the corresponding amine and 4 drops of dry THF to homogenize the mixture. It is heated to low THF reflux
    Argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with
    Water. The organic phase is dried with Na2SO4, filtered and the solvent is removed at
    reduced pressure It is purified by silica gel column chromatography.


    using a mixture of dichloromethane: hexane (1: 1) as eluent unless otherwise indicated.
    Method 2: Synthesis of 1.6 (7) -di [alkyl (aryl) amino] perylene-3,4: 9,10
    5, N'-disubstituted tetracarboxyidiimide In a 10 mL round bottom flask 0.2 mmol of perylene-3,4: 9,10 N, N'-disubstituted tetracarboxyidimide are dissolved in 4 mL of dry THF. Then 0.48 mmol of the corresponding amine and 0.48 mL of TBAF (1M solution in THF, 0.48 mmol) are added. It is heated under reflux of THF under an argon atmosphere for 24 hours. He
    10 crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by silica gel column chromatography and using a mixture of dichloromethane: hexane (1: 1) as eluent, unless otherwise indicated.
    Method 3: 1,6,7-tri [alkyl (aryl) amino] perylene-3,4: 9,10-tetracarboxyidiimide N, N-substituted N and [1,12-dialkyl (aryl) amino] perylene-3, 4: 9,10-tetracarboxyidimide N, N-substituted N To a 5 mL heart flask are added 0.2 mmol perylene-3,4: 9,10 tetracarboxyidiimide N, N'-disubstituted, 1.2 mL fluoride tetrabutylammonium (solution
    1M in THF, 1.2 mmol), 3.2 mmol of the corresponding amine (16 eq) and 4 drops of dry THF to homogenize the mixture. It is heated under reflux of THF under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and used
    A mixture of dichloromethane: hexane (1: 1) as eluent, unless otherwise indicated.
    Example 23: N, N’-bis (1’-hexylheptyl) -1- (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxidiimide (23)


    Compound 23 is obtained following method 1. Amine: piperidine. Yield: 53%. 1H-NMR (CDCl3) į 0.82 (t, 12H, CH3), 1.27 (broad s, 34H, CH2 and CH2 piperidine),
    5.85 (m, 8H, CH2 and CH2 piperidine), 2.26 (m, 4H, CH2), 2.96 (m, 2H, CH2 piperidine), 3.49 (m, 2H, CH2 piperidine), 5.20 (m, 2H, N-CH), 8.57 (m, 6H, ArH), 9.87 (d, 1H, ArH); MALDI-TOF MS m / z:> M + @ theoretical C55H71N3O4: 837.54, experimental: 837.52; IR (KBr) (cm-1): 2,952, 2,925, 2,854, 1,695, 1,654, 1,589, 1,409, 1,330, 1,249; UV-vis (CHCl3) Ȝmax / nm (log İ): 447 (4.25), 601 (4.35).
    10 Example 24: N, N’-bis (1’-hexylheptyl) -1,6,7-tri (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxyidiimide (24)


    OR NOT
    N N
    N
    OR NOT
    Compound 24 is obtained according to method 3. Amine: piperidine. Yield: 55%.
    1H-NMR (CDCl3) į 0.83 (t, 12H, CH3), 1.26 (broad s, 40H, CH2 and CH2 piperidine), 1.70 (m,
    4H, CH2 piperidine), 1.89 (m, 14H, CH2 and CH2 piperidine), 2.27 (m, 4H, CH2), 2.41 (t, 1H, CH2
    5 piperidine) 3.22 (m, 2H, CH2 piperidine), 3.46 (m, 2H, CH2 piperidine), 3.66 (m, 1H, CH2 piperidine), 4.22 (m, 2H, CH2 piperidine) , 5.21 (m, 2H, N-CH), 8.36 (m, 1H, ArH), 8.44 (m, 2H, ArH), 8.57 (m, 1H, ArH), 9.84 (d, 1H, ArH); MALDI-TOF MS m / z:> M + @ theoretical C65H89N5O4: 1,003.69, experimental: 1,003.68; IR (KBr) (cm-1): 2,925, 2,854, 1,687, 1,650, 1,585, 1,452, 1,438, 1,413, 1,380, 1,334, 1,305, 1,265, 1,257; UV-vis (CHCl3) Ȝmax / nm (log İ):
    10 571 (4.16), 708 (4.52)
    Example 25: N, N’-bis (1’-hexylheptyl) -1,12-di (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxyidiimide (25)


    Compound 25 is obtained according to method 3. Amine. Piperidine Yield: 13%.1H-NMR (CDCl3) į 0.83 (t, 12H, CH3), 1.26 (broad s, 36H, CH2 and CH2 piperidine), 1.47 (m,5 4H, CH2 piperidine), 1.74 (m, 2H, CH2 piperidine), 1.89 (m, 6H, CH2 and CH2 piperidine), 2.00 (m,2H, CH2 piperidine), 2.13 (t, 2H, CH2 piperidine), 2.29 (m, 4H, CH2), 3.48 (t, 2H, Į-CH2piperidine), 4.32 (m, 2H, CH2 piperidine), 5.24 (m, 2H, N-CH), 8.58 (m, 4H, ArH), 8.64 (m, 2H,ArH). MALDI-TOF MS m / z:> M + @ theoretical C60H80N4O4: 920.62, experimental: 920.39. GO(KBr) (cm-1): 2,954, 2,925, 2,854, 1,689, 1,652, 1,585, 1,461, 1,438, 1,411, 1,376,
    10 1,307, 1,259, 806. UV-vis (CHCl3) Ȝmax / nm (log İ): 436 (3.97), 556 (4.01), 676 (4.43).
    Example 26: N, N’-bis (1’-hexylheptyl) -1.6 (7) -di (piperidin-N-yl) perylene-3.4: 9,10 tetracarboxyidiimide (26)


    ORNO ONO
    N
    N
    N
    N
    ONO ONO
    Compound 26 is obtained according to method 2. Amine: piperidine. Yield: 30% (67% isomer 1.6; 33% isomer 1.7 approx.). 1H-NMR (CDCl3) į 0.83 (t, 12H, CH3), 1.26 (broad s, 36H, CH2 and CH2 piperidine), 1.80 (m, 12H, CH2 and CH2 piperidine), 2.25 ( m, 4H,
    5 CH2), 2.93 (m, 4H, CH2 piperidine), 3.39 (m, 2H, CH2 piperidine), 3.54 (m, 2H, CH2 piperidine), 5.19 (m, 2H, N- CH), 8.58 (m, 4H, ArH), 9.68 (1.6 isomer) (d, 1H, ArH), 9.74 (1.7 isomer) (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C60H80N4O4: 920.62, experimental: 920.39. IR (KBr) (cm-1): 2,924, 2,853, 1,692, 1,653, 1,584, 1,451, 1,411, 1,338, 1,321, 1,249, 1,219, 809. UV-vis (CHCl3) Ȝmax / nm (log İ): 400 ( 4.04), 435 (3.91), 659 (4.36).
    10 Example 27: N, N’-bis (1’-hexylheptyl) -1.6 (7) -di (morpholin-N-yl) perylene-3.4: 9,10 tetracarboxyidiimide (27)


    Compound 27 is obtained following method 3. Amine: Morpholine. Eluent used in column chromatography: dichloromethane to obtain 27 followed by dichloromethane: ethyl acetate (9: 1) to obtain 28. Yield: 22% (50% isomer 5 1.6; 50% isomer 1.7 approx.) . 1H-NMR (CDCl3) į 0.84 (t, 12H, CH3), 1.26 (broad s, 32H, CH2), 1.86 (m, 4H, CH2), 2.26 (m, 4H, CH2 ), 3.14 (m, 4H, CH2 morpholine), 3.30 (d, 2H, CH2 morpholine), 3.46 (d, 2H, CH2 morpholine), 3.96 (m, 8H, CH2 morpholine), 5.19 (m, 2H, N-CH), 8.47 (m, 4H, ArH), 9.84 (1.6 isomer) (d, 1H, ArH), 9.90 (1.7 isomer) (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C58H76N4O6: 924.58, experimental: 924.12. IR (KBr) (cm
    10 1): 2,958, 2,923, 2,854, 1,693, 1,652, 1,594, 1,585, 1,413, 1,334, 1,322, 1,259, 1,118, 1,093, 1,024. UV-vis (CHCl3) Ȝmax / nm (log İ): 400 (3.92), 426 (3.95), 640 (4.31).
    Example 28: N, N’-bis (1’-hexylheptyl) -1,6,7-tri (morpholin-N-yl) perylene-3,4: 9,10 tetracarboxidiimide (28)


    Compound 28 is obtained by method 3. Amine: morpholine. Eluent used in column chromatography: dichloromethane to obtain 27 followed by dichloromethane: ethyl acetate (9: 1) to obtain 28. Yield: 40%. 1H-NMR 5 (CDCl3) į 0.84 (t, 12H, CH3), 1.26 (broad s, 32H, CH2), 1.88 (m, 6H, CH2 and CH2 morpholine), 2.26 (m , 6H, CH2 and CH2 morpholine), 2.45 (m, 1H, CH2 morpholine), 2.65 (m, 1H, CH2 morpholine), 3.17 (m, 2H, CH2 morpholine), 3.37 (m , 2H, CH2 morpholine), 3.51 (m, 2H, CH2 morpholine), 3.80 (m, 4H, CH2 morpholine), 4.09 (m, 8H, CH2 morpholine), 5.21 (m, 2H , N-CH), 8.48 (m, 4H, ArH), 9.82 (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C62H83N5O7: 1,009.63,
    10 experimental: 1,009.09. IR (KBr) (cm-1): 2,954, 2,923, 2,853, 1,689, 1,651, 1,585, 1,457, 1,415, 1,364, 1,332, 1,305, 1,254, 1,114. UV-vis (CHCl3) Ȝmax / nm (log İ): 556 (4.23), 681 (4.53).
    Example 29: N, N’-bis (1’-hexylheptyl) -1- (4-methylpiperazin-1-yl) perylene-3,4: 9,1015 tetracarboxyidiimide (29)


    OR NOT
    N
    N
    OR NOT
    Compound 29 is obtained following method 3. Amine: 1-Methylpiperazine. Eluent used in column chromatography: dichloromethane: ethyl acetate (1: 2). Yield: 43%. 1H-NMR (CDCl3) į 0.83 (t, 12H, CH3), 1.28 (broad s, 32H, CH2), 5.85 (m, 4H, CH2), 2.23 (m, 4H, CH2), 2.53 (s, 3H, CH3 piperazine), 2.69 (m, 2H, CH2 piperazine), 3.00 (m, 2H, CH2 piperazine), 3.27 (m, 2H, CH2 piperazine) , 3.52 (m, 2H, CH2 piperazine), 5.18 (m, 2H, N-CH), 8.60 (m, 6H, ArH), 9.93 (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C55H72N4O4: 852.56, experimental: 852.08. IR (KBr) (cm-1): 2,952, 2,925, 2,854, 1,695, 1,654, 1,589, 1,459, 1,409, 1,332, 1,249, 809. UV-vis (CHCl3) Ȝmax / nm (log İ):
    10 446 (3.16), 591 (3.34).
    Example 30: N, N’-bis (1’-hexylheptyl) -1,6-di (4-methylpiperazin-1-yl) perylene-3,4: 9,10 tetracarboxyidiimide (30)


    OR NOT
    N
    N
    N
    N
    ON
    Compound 30 is obtained following method 3 Amine: 1-Methylpiperazine.
    Yield: 19%. 1H-NMR (CDCl3) į 0.84 (t, 12H, CH3), 1.26 (broad s, 32H, CH2),
    1.87 (m, 4H, CH2), 2.25 (m, 4H, CH2), 2.51 (s, 6H, CH3 piperazine), 2.63 (m, 4H, CH2
    5 piperazine), 2.96 (m, 4H, CH2 piperazine), 3.18 (m, 4H, CH2 piperazine), 3.42 (m, 4H, CH2 piperazine), 5.21 (m, 2H, N- CH), 8.40 (s, 2H, ArH), 8.62 (m, 2H, ArH), 9.77 (d, 2H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C60H82N6O4: 950.64, experimental: 950.40. IR (KBr) (cm1): 2,924, 2,852, 1,693, 1,653, 1,585, 1,460, 1,426, 1,339, 1,319, 1,261, 1,246, 1,142. UV-vis (CHCl3) Ȝmax / nm (log İ): 634 (4.30).
    10 Example 31: N, N’-bis (1’-hexylheptyl) -1,7-di (4-methylpiperazin-1-yl) perylene-3,4: 9,10 tetracarboxidiimide


    Compound 31 is obtained following method 3. Amine: 1-methylpiperazine. Yield: 5%. 1H-NMR (CDCl3) į 0.83 (t, 12H, CH3), 1.25 (broad s, 32H, CH2), 5.83 (m, 4H, CH2), 2.23 (m, 4H, CH2), 2.56 (s, 6H, CH3 piperazine), 2.70 (m, 4H, CH2 piperazine), 3.02 (m, 4H, CH2 piperazine), 3.31 (m, 4H, CH2 piperazine) , 3.59 (m, 4H, CH2 piperazine), 5.18 (m, 2H, N-CH), 8.46 (m, 4H, ArH), 9.69 (d, 2H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C60H82N6O4: 950.64, experimental: 950.89. IR (KBr) (cm-1): 2,954, 2,925, 2,854, 1,693, 1,652, 1,594, 1,583, 1,413, 1,340, 1,324, 1,255. UV-vis (CHCl3) Ȝmax / nm (log İ): 10 429 (3.82), 661 (3.96).
    Example 32: N, N’-di- (1’-hexylheptyl) -1- (phenylamino) -3.4: 9,10-tetracarboxyidiimide
    (32)


    Compound 32 is obtained by method 1. Amine: Aniline. Yield: 72%. 1H-NMR (CDCl3) į 0.82 (t, 12H, CH3), 1.25 (broad s, 32H, CH2), 1.85 (m, 4H, CH2), 2.20 (m, 4H, CH2 ), 5.50 (m, 2H, N-CH), 6.94 (broad s, 1H, NH) 7.17 (m, 3H, ArH), 7.41
    5 (m, 1H, ArH), 8.50 (m, 4H, ArH), 8.65 (m, 2H, ArH), 9.17 (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C56H67N3O4: 845.51, experimental: 845.31. IR (KBr) (cm-1): 3,319, 2,954, 2,924, 2,854, 1,694, 1,654, 1,589, 1,418, 1,332, 1,270, 1,248. UV-vis (CHCl3) Ȝmax / nm (log İ): 449 (3.81), 606 (3.93).
    10 Example 33: N, N’-bis (1’-cyclohexyl) -1,6-di (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxidiimide (33)


    Compound 33 is obtained following method 1. Amin: Piperidine. Eluent used in column chromatography: dichloromethane: hexane (9: 1). Yield: 19%. 1H-NMR (CDCl3) į 1.45 (m, 10H, CH2 and CH2 piperidine), 1.77-1.89 (m, 18H, CH2 and CH2 piperidine),
    5 2.58 (m, 4H, CH2), 2.86 (m, 4H, CH2 piperidine), 3.37 (m, 4H, CH2 piperidine), 5.05 (m, 2H, N-CH), 8 , 37 (s, 2H, ArH), 8.58 (d, 2H, ArH), 9.73 (d, 2H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C46H48N4O4: 720.37, experimental: 719.83. L. Fan, Y. Xu and H. Tian; Tetrahedron Lett. 2005, 46, 4443-4447.
    10 Example 34: N, N’-bis (1’-cyclohexyl) -1,7-di (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxidiimide (34)
    Compound 34 is obtained following method 1. Amin: Piperidine. Eluent used in column chromatography: dichloromethane: hexane (9: 1). Yield: 9%. 1 HOUR


    NMR (CDCl3) į 1.46 (m, 10H, CH2 and CH2 piperidine), 1.76-1.94 (m, 18H, CH2 and CH2 piperidine), 2.58 (m, 4H, CH2), 2.91 (m, 4H, CH2 piperidine), 3.48 (m, 4H, CH2 piperidine), 5.05 (m, 2H, N-CH), 8.38 (d, 2H, ArH), 8.44 (d , 2H, ArH), 9.61 (d, 2H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C46H48N4O4: 720.37, experimental: 720.21. L. Fan, Y. Xu and H. Tian; Tetrahedron Lett. 2005, 46, 4443-4447.
    Example 35: N, N’-bis (1’-cyclohexyl) -1,6,7-tri (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxidiimide (35)
    Compound 35 is obtained following method 1. Amine: Piperidine. Eluent used in column chromatography: dichloromethane: hexane (9: 1). Yield: 4%. 1H-NMR (CDCl3) į 1.41 (m, 12H, CH2 and CH2 piperidine), 1.61-2.19 (m, 26H, CH2 and CH2 piperidine), 2.40 (m, 1H, CH2 piperidine), 2.62 (m, 4H, CH2), 3.20 (m, 2H, CH2 piperidine), 3.46 (m, 2H, CH2 piperidine), 3.64 (m, 1H, CH2 piperidine), 4.19 (m, 2H, CH2 piperidine), 5.10 (m, 2H, N-CH),
    8.34 (s, 1H, ArH), 8.44 (d, 2H, ArH), 8.54 (s, 1H, ArH), 9.83 (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C51H57N5O4: 803.44, experimental: 802.89. IR (KBr) (cm-1): 2,927, 2,852, 1,687, 1,650, 1,581, 1,450, 1,440, 1,413, 1,334, 1,305, 1,259, 1,022,
    804. UV-vis (CHCl3) Ȝmax / nm (log İ): 577 (4.04), 706 (4.37).
    Example 36: N, N’-bis (1’-cyclohexyl) -1- (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxyidiimide (36)


    Compound 36 is obtained following method 1. Amin: Piperidine. Eluent used
    in column chromatography: dichloromethane: hexane (9: 1). Yield: 5%. 1 HOUR-
    NMR (CDCl3) į 1.46 (m, 8H, CH2 and CH2 piperidine), 1.76 (m, 8H, CH2 and CH2 piperidine), 1.85
    5 (m, 6H, CH2 and CH2 piperidine), 2.58 (m, 4H, CH2), 2.92 (m, 2H, CH2 piperidine), 3.44 (m, 2H, CH2 piperidine), 5.06 (m, 2H, N-CH), 8.48 (m, 3H, ArH), 8.54 (s, 1H, ArH), 8.59 (d, 1H, ArH), 8.62 (d, 1H , ArH), 9.82 (d, 1H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C41H39N3O4: 637.29, experimental: 636.96. K-Y. Chen, T-C. Fang and M-J. Chang; Dyes Pigments. 2011, 92, 517-523.
    10 Example 37: N, N’-bis (1’-cyclohexyl) -1,12-di (piperidin-N-yl) perylene-3,4: 9,10 tetracarboxidiimide (37)


    Compound 37 is obtained following method 1. Amin: Piperidine. Eluent used in column chromatography: dichloromethane: hexane (9: 1). Yield: 8%. 1H-NMR (CDCl3) į 1.45 (m, 12H, CH2 and CH2 piperidine), 1.65-2.02 (m, 18H, CH2 and CH2 piperidine), 2.11 (m, 2H, CH2 piperidine), 2.62 (m, 4H, CH2), 3.49 (m, 2H, CH2 piperidine), 4.30 (m, 2H,
    5 CH2 piperidine), 5.11 (m, 2H, N-CH), 8.54 (m, 4H, ArH), 8.64 (s, 2H, ArH). MALDI-TOF MS m / z:> M + @ theoretical C46H48N4O4: 720.37, experimental: 719.86. IR (KBr) (cm-1): 2,923, 2,852, 1,689, 1,650, 1,585, 1,438, 1,409, 1,375, 1,307, 1,259, 1,022, 804. UV-vis (CHCl3) Ȝmax / nm (log İ): 417 ( 3.79), 437 (3.82), 558 (3.87), 674 (4.20). 10 RENT-POI
    Method 1: Synthesis of 1-aquylthioperylene-3,4: 9,10-tetracarboxyidiimide
    In a heart-shaped flask 0.1 mmol of perylene-3.4: 9.10 tetracarboxyidiimide is dissolved in 0.3 mL of dry THF. Then 0.4 mmol of the
    15 corresponding thiol, 0.24 mmol of potassium fluoride and 0.48 mmol of 18-crown-6. It is heated at 70 ° C under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent.
    Method 2: Synthesis of 1,6 (7) -dialkylthioperylene-3,4: 9,10-tetracarboxyidiimide
    In a round bottom flask, 0.1 mmol of perylene-3.4: 9.10 tetracarboxyidiimide are dissolved in 2 mL of dry THF. Then 1.4 mmol of the corresponding thiol, 0.36 mmol of potassium fluoride and 0.72 mmol of 18-crown-6 are added. Be
    25 heats under reflux of THF under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent.
    Method 3: Synthesis of 2,5,8-trialkylthio-11-bromoperylene-3,4: 9,10-tetracarboxyidiimide and 2,5-dialkitio-8,11-dibromoperylene-3,4: 9,10-tetracarboxyidiimide In a bottom flask round, 0.05 mmol of 2,5,8,11 tetrabromoperylene-3,4: 9,10-tetracarboxyidiimide are dissolved in 2 mL of dry THF. Then
    0.25 mmol of the corresponding thiol 0.25 mmol of potassium fluoride and 0.5 mmol of 18-crown-6 are added. It is heated under reflux of THF under an argon atmosphere for 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase dries


    With Na2SO4, filter and remove the solvent under reduced pressure. It is purified by column chromatography with silica gel and dichloromethane: hexane 1: 1 as eluent.
    5 Method 4: Synthesis of 2,5,8,11-tetraalkylthioperylene-3,4: 9,10-tetracarboxyidiimideIn a round bottom flask, 0.03 mmol of 2,5,8,11 tetrabromoperylene-3,4: 9,10-tetracarboxy diimide are dissolved in 2 mL of dry THF. Then0.21 mmol of the corresponding thiol, 0.20 mmol of potassium fluoride and 0.40 are addedmmol of 18-crown-6. It is heated at reflux of THF under argon atmosphere for
    10 24 hours. The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and chloroform: hexane 1: 1 as eluent.
    Method 5: Synthesis of 1-alkoxy-6 (7) -alkylthioperylene-3,4: 9,10-tetracarboxyidiimide 0.1 mmol of 1-alkylthioperylene-3,4: 9,10 tetracarboxidiimide are dissolved in a round bottom flask in 2 mL of dry THF. Then 1.4 mmol of the corresponding alcohol and 0.36 mmol of TBAF (1M solution in THF) are added. It is heated under reflux of THF under an argon atmosphere for 24 hours. The crude dissolves in
    20 CH2Cl2 and wash with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent.
    Method 6: synthesis of 2-alkoxy-5,8,11-trialkylthioperylene-3,4: 9,10
    Tetracarboxyidimide In a round bottom flask, 0.025 mmol of 2-bromo-5,8,11 trialkylthioperylene-3,4: 9,10-tetracarboxyidiimide is dissolved in 0.5 mL of dry THF. Then 0.175 mmol of the corresponding alcohol, 0.12 mmol of TBAF (1M solution in THF) are added. It is heated under reflux of THF under an argon atmosphere for 24 hours.
    The crude is dissolved in CH2Cl2 and washed with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and chloroform: hexane 1: 1 as eluent.
    Method 7: Synthesis of 1-alkylthioperylene-3,4: 9,10-tetracarboxyidiimide and 1,6 (7) 35 dialkylthioperylene-3,4: 9,10-tetracarboxyidiimide


    In a round bottom flask, 0.1 mmol of perylene-3.4: 9.10 tetracarboxyidiimide are dissolved in 2 mL of dry THF. Then 1.2 mmol of the corresponding thiol, 0.36 mmol of cesium fluoride and 1.44 mmol of 18-crown-6 are added. It is heated under reflux of THF under an argon atmosphere for 24 hours. The oil is
    5 dissolve in CH2Cl2 and wash with water. The organic phase is dried with Na2SO4, filtered and the solvent is removed under reduced pressure. It is purified by column chromatography with silica gel and toluene as eluent.
    Example 38: N, N’-di- (1’-hexylheptyl) -1.6 (7) -dihexylthioperylene-3.4: 9,1010 tetracarboxyidiimide (38)
    Compound 38 is obtained by method 7. Yield: 35%. 1H NMR (300MHz, CDCl3) į 0.82 (m, 18H), 1.25 (broad s, 40H), 1.44 (m, 4H), 1.68 (m, 4H), 1.87(m, 4H), 2.28 (m, 4H), 3.22 (t, 4H), 5.20 (m, 2H), 8.68 (s, 2H), 8.76 (s, 2H) , 8.85 (m,15 2H). 13C NMR (CDCl3) į 13.79, 13.90, 22.26, 22.45, 26.79, 28.27, 28.39, 29.09, 31.09,31.63, 32.30, 35.83, 54.67, 121.89, 122.60, 125.54, 128.37, 128.81, 130.59, 131.30,132.32, 132.58, 138.42, 163.57, 164.53. MALDI-TOF MS m / z. > Theoretical M + @C62H86N2O4S2 986.60, experimental 986.78. IR (KBr): 2949, 2926, 2856, 1695, 1660,1584, 1461, 1409, 1321, 1240, 802, 750 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 20 430 (4.2), 565 (4.6).
    Alternatively, compound 38 is obtained following method 2. Yield: 82%.


    Example 39: N, N’-di- (1’-hexylheptyl) -1-hexylthioperylene-3,4: 9,10-tetracarboxy diimide
    (39)
    5 Compound 39 is obtained by method 7. Yield: 32%. 1H NMR (300 MHz, CDCl3) į 0.82 (m, 15H), 1.26 (broad s, 36H), 1.46 (m, 2H), 1.72 (m, 2H), 1.86 ( m, 4H), 2.25 (m, 4H), 3.25 (t, 2H), 5.20 (m, 2H), 8.62 (m, 6H), 8.94 (d, 1H). 13C NMR (CDCl3) į 13.90, 14.01, 22.38, 22.56, 26.91, 26.92, 28.36, 28.53, 29.19, 29.21, 31.22, 31.74, 32.37, 36.18, 54.66, 54.81, 122.34, 122.71, 123.06, 123.46, 126.50, 127.06,
    10 127.77, 128.91, 129.17, 130.45, 131.22, 132.69, 133.34, 133.96, 139.82, 163.51, 164.52. MALDI-TOF MS m / z. > M + @ theoretical C56H74N2O4S 870.54, experimental 870.59. IR (KBr): 2955, 2920, 2856, 1689, 1660, 1578, 1450, 1391, 1327, 8142, 738 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 445 (4.2), 543 (4.6).
    Alternatively, compound 39 is obtained following method 1. Yield: 41%.
    Example 40: N, N’-di- (1’-hexylheptyl) -1-s-butylthioperylene-3,4: 9,10 tetracarboxyidiimide (40)


    Compound 40 is obtained following method 1. Yield: 33% (50% with method 2 after 3 days). 1H NMR (300 MHz, CDCl3) į 0.82 (m, 12H), 1.04 (t, 3H), 1.27 (broad s, 32H), 1.61 (m, 3H), 1.75 ( m, 1H), 1.86 (m, 4H), 2.25 (m, 4H), 3.66 (m, 2H), 5.20 (m, 2H), 8.65-8.82 ( m, 6H), 8.99 (d, 1H). 13C NMR (CDCl3) į 11.4, 14.02, 20.47, 22.56, 22.57, 26.91, 29.18, 29.22, 29.41, 29.54, 29.60, 31.74, 31.75, 32.38, 47.04, 54.68, 63.10, 122.45, 123.48, 126.80, 127.11, 127.96, 128.89, 129, 79, 130.39, 131.19, 133.52, 134.00, 138.67, 163.63, 164.56. MALDI-TOF MS m / z,> M + H + @ theoretical C54H70N2O4S 842.51, experimental 842.51. IR (KBr): 2921, 2851, 1695, 1662, 1589,
    10 1462, 1397, 1343, 1241, 1070, 808, 747 cm -1. UV Vis (CH2Cl2), Omax / nm (log H): 450 (4.0), 535 (4.4).
    Example 41: N, N’-di- (1’-hexylheptyl) -1.6 (7) -di-s-butylthioperylene-3,4: 9,10 tetracarboxyidiimide (41)


    Compound 41 is obtained by method 2. Yield: 20% (the proportion of each isomer cannot be determined). 1H NMR (300 MHz, CDCl3) į 0.82 (m, 12H), 1.04 (t, 6H), 1.29 (broad s, 32H), 1.59 (m, 6H), 1.75 ( m, 2H), 1.86 (m, 4H), 2.24 5 (m, 4H), 3.64 (m, 4H), 5.20 (m, 2H), 8.67-8.89 ( m, 6H). 13C NMR (CDCl3) į 11.43, 11.53, 14.03, 20.49, 22.57, 26.92, 29.21, 29.39, 29.69, 31.75, 32.43, 46.53, 46.58, 54.74, 122.06, 125.79, 125.81, 128.61, 129.40, 129.96, 132.26, 132.70, 133.37, 137, 52, 138.73, 163.62, 164.75. MALDI-TOF MS m / z,> M + H + @ theoretical C58H78N2O4S2 930.54, experimental 930.58. IR (KBr): 2925, 2855, 1695, 1654, 1585, 1458, 1397,
    10 1319, 1249, 1172, 808 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 445 (4.0), 557 (4.4).
    Example 42: N, N’-di- (1’-hexylheptyl) -1.6 (7) -di-t-butylthioperylene-3,4: 9,10
    tetracarboxyidiimide (42)


    Compound 42 is obtained following method 1. Yield: 21% (81% isomer 1.6; 9% isomer 1.7 approx.). 1H NMR (300 MHz, CDCl3) į 0.82 (m, 12H), 1.27 (broad s, 50H), 1.88 (m, 4H), 2.24 (m, 4H), 5.18 ( m, 2H), 8.64 (s, 2H), 8.96 (s, 2H), 9.33
    5 (d, 1H), 9.43 (d, 1H). 13C NMR (CDCl3) į 14.02, 22.57, 26.95, 29.20, 31.04, 31.74, 32.39, 50.88, 54.79, 122.38, 123.16, 127.15, 128.44, 129.41, 130.01, 131.61, 133.61, 13367, 138.05, 139.75, 140.61, 163.46, 164.60. MALDI-TOF MS m / z,> M + H + @ theoretical C58H78N2O4S2 930.54, experimental 930.62. IR (KBr): 2926, 2850, 1706, 1660, 1584, 1450, 1403, 1316, 1246, 1176, 802 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 545 (4.6).
    Example 43: N, N’-di- (1’-hexylheptyl) -1-t-butylthioperylene-3,4: 9,10
    tetracarboxyidiimide (43)


    Compound 43 is obtained following method 1. Yield: 12%. 1H NMR (300 MHz, CDCl3) į 0.82 (m, 12H), 1.27 (broad s, 41H), 1.87 (m, 4H), 2.24 (m, 4H), 5.18 ( m, 2H), 8.65 (m, 5H), 8.96 (s, 1H), 9.80 (d, 1H). 13C NMR (CDCl3) į 14.02, 22.55,
    5 22.57, 26.93, 29.17, 29.21, 29.68, 31.14, 31.74, 32.40, 51.52, 54.74, 122.82, 123.37, 127 , 16, 128.05, 128.47, 128.78, 130.89, 131.20, 131.88, 133.85, 134.30, 163.66, 164.32. MALDI-TOF MS m / z,> M + @ theoretical C54H70N2O4S 842.51, experimental 842.53 IR (KBr): 2926, 2862, 1701, 1660, 1578, 1461, 1397, 1333, 1251, 808, 750. UV Vis (CH2Cl2), Omax / nm (log H): 496 (4.4), 530 (4.6).
    10 Example 44: N, N’-di- (1’-hexylheptyl) -1.6 (7) -dioctylthioperylene-3.4: 9,10 tetracarboxyidiimide (44)


    44 Compound 44 is obtained following method 2. Yield: 71% (75% isomer 1.6; 25% isomer 1.7 approx.). 1H NMR (300 MHz, CDCl3) į 0.83 (m, 18H), 1.24 (broad s, 48H), 1.43 (m, 4H), 1.69 (m, 4H), 1.87 ( m, 4H), 2.24 (m, 4H), 3.22 (t, 4H), 5.20
    5 (m, 2H), 8.67 (m, 2H), 8.76 (m, 2H), 8.85 (m, 2H). 13C NMR (CDCl3) į 14.03, 22.57, 26.92, 28.42, 28.84, 28.87, 29.01, 29.02, 29.19, 29.22, 29.25, 31.69, 31.76, 32.43, 35.98, 54.78, 121.43, 122.00, 123.17, 125.65, 127.82, 128.05, 128.49, 128, 93, 130.59, 131.48, 132.43, 132.68, 138.57, 163.59, 164.68. MALDI-TOF MS m / z,> M + H + @ theoretical C66H94N2O4S2 1042.67, experimental 1042.71. IR (KBr): 2920, 2838, 1701, 1654, 10 1592, 1461, 1397, 1321, 1240, 808 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 430 (4.2), 564 (4.6).
    Example 45: N, N’-di- (1’-hexylheptyl) -1-octylthioperylene-3,4: 9,10-tetracarboxyidiimide
    (Four. Five)


    Compound 45 is obtained following method 1. Yield: 43%. 1H NMR (300MHz, CDCl3) į 0.82 (m, 15H), 1.25 (broad s, 40H), 1.46 (m, 2H), 1.72 (m, 2H), 1.87(m, 4H), 2.24 (m, 4H), 3.25 (t, 2H), 5.18 (m, 2H), 8.64 (m, 6H), 8.96 (d, 1H) . 13C NMR5 (CDCl3) į 14.02, 22.57, 26.91, 28.40, 28.85, 29.02, 29.03, 29.19, 29.22, 31.70, 31.74,31.75, 32.39, 36.24, 54.68, 122.39, 123.52, 126.54, 127.11, 127.82, 128.94, 129.23,130.55, 131.28, 132.79, 133.41, 134.03, 134.23, 139.87, 163.59, 164.58. EM MALDI-TOF m / z,> M + H + @ theoretical C58H78N2O4S 898.57, experimental 898.54. IR (KBr): 2926,2862, 1706, 1654, 1590, 1456, 1415, 1345, 1246, 802, 750 cm-1. UV Vis (CH2Cl2),
    10 Omax / nm (log H): 445 (4.1), 543 (4.5).
    Example 46: N, N’-di- (1’-hexylheptyl) -1-decylthioperylene-3,4: 9,10-tetracarboxy diimide
    (46)


    Compound 46 is obtained following method 1. Yield: 40%. 1H NMR (300MHz, CDCl3) į 0.82 (m, 15H), 1.23 (broad s, 44H), 1.43 (m, 2H), 1.73 (m, 2H), 1.87(m, 4H), 2.25 (m, 4H), 3.25 (t, 2H), 5.20 (m, 2H), 8.61 (m, 6H), 8.95 (d, 1H) . 13C NMR5 (CDCl3) į 14.01, 14.05, 22.56, 22.61, 26.91, 26.92, 28.39, 28.85, 29.07, 29.19, 29.21,29.22, 29.36, 29.44, 31.74, 31.81, 32.37, 36.20, 54.66, 122.32, 123.44, 126.48,127.04, 127.75, 128.89, 129.16, 130.42, 131.28, 133.31, 133.94, 134.17, 139.86,163.51, 164.61. MALDI-TOF MS m / z,> M + @ theoretical C60H82N2O4S 926.59, experimental926.76. IR (KBr): 2961, 2961, 2926, 2850, 1689, 1660, 1601, 1456, 1391, 1339, 1240,
    10 802, 738 cm -1. UV Vis (CH2Cl2), Omax / nm (log H): 446 (4.3), 542 (4.7).
    Example 47: N, N’-di- (1’-hexylheptyl) -1.6 (7) -didecylthioperylene-3.4: 9,10 tetracarboxidiimide (47)


    Compound 47 is obtained following method 2. Yield: 62%. (The proportion of each isomer cannot be determined). 1H NMR (300 MHz, CDCl3) į 0.82 (m, 18H), 1.22 (broad s, 56H), 1.4, (m, 4H), 1.69 (m, 4H), 1.87 (m, 4H), 2.25 (m, 4H), 3.22 5 (t, 4H), 5.20 (m, 2H), 8.66 (m, 2H), 8.75 (m, 2H ), 8.84 (m, 2H). 13C NMR (CDCl3) į 14.02, 14.06, 22.57, 22.62, 26.92, 28.43, 28.85, 29.07, 29.22, 29.36, 29.45, 31.76, 31.82, 32.42, 35.96, 54.72, 121.41, 121.84, 122.17, 122.66, 123.15, 125.63, 127.87, 128, 04, 128.48, 128.89, 128.95, 129.35, 130.58, 131.42, 132.36, 132.67, 138.58, 139.89, 163.66, 164.69. MALDI-TOF MS m / z,> M + @ theoretical C70H102N2O4S2 1098.73,
    10 experimental 1098.54. IR (KBr): 2949, 2943, 2838, 1689, 1654, 1584, 1473, 1397, 1321, 1240, 1321, 802, 744 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 429 (4.3), 566 (4.65).
    Example 48: N, N’-di- (1’-hexylheptyl) -1.6 (7) -dibenzylthioperylene-3.4: 9,1015 tetracarboxidiimide (48)


    Compound 48 is obtained by method 2. Yield: 20% (The proportion of each isomer cannot be determined). 1H NMR (300 MHz, CD2Cl2) į 0.83 (t, 12H), 1.26 (broad s, 32H), 1.85 (m, 4H), 2.27 (m, 4H), 4.40 ( s, 4H), 5.17 (m, 2H), 7.16 5 (m, 6H), 7.26 (m, 4H), 8.58 (broad s, 2H), 8.85 (d, 4H ). 13C NMR (CDCl3) į 14.23, 1.29, 23.02, 23.11, 27.29, 29.65, 2965, 30.07, 30.11, 32.22, 32.35, 32, 78, 41.27, 125.28, 126.42, 127.98, 128.78, 128.92, 129.59, 133.05, 135.83, 137.51, 163.56, 164.93. MALDI-TOF MS m / z,> M + 1 + @ theoretical C64H74N2O4S2 999.51, experimental 999.58. IR (KBr): 2938, 2850, 1689, 1654, 1590, 1397, 1321, 1246, 709 cm-1. UV Vis
    10 (CH2Cl2), Omax / nm (log H): 455 (4.1), 531 (4.4), 555 (4.4).
    Example 49: N, N’-di- (1’-hexylheptyl) -1-benzylthioperylene-3,4: 9,10 tetracarboxidiimide (49)


    Compound 49 is obtained by method 1. Yield: 30%. 1H NMR (300 MHz, CDCl3) į 0.83 (t, 12H), 1.24 (broad s, 32H), 1.87 (m, 4H), 2.24 (m, 4H), 4.47 ( s, 2H), 5.19 (m, 2H), 7.23 (m, 3H), 7.34 (d, 2H), 8.64 (m, 6H), 8.88 (m, 2H). 13C NMR 5 (CD2Cl3) į 14.23, 14.24, 23.02, 27.33, 29.66, 32.22, 32.78, 41.37, 122.89, 123.91, 127.16 , 127.36, 128.15, 129.04, 129.26, 129.70, 129.76, 133.56, 133.76, 134.23, 34.37, 135.57, 138.81, 163 , 80, 164.82. MALDI-TOF MS m / z,> M + H + @ theoretical C57H68N2O4S 877.49, experimental 877.50. IR (KBr): 2920, 2850, 1712, 1642, 1596, 1450, 1327, 1240, 808, 744 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 444 (4.3) 542 (4.7).
    10 Example 50: N, N’-bis- (di-2 ’, 5’-t-butylphenyl) -1.6 (7) -dihexylthioperylene-3,4: 9,10 tetracarboxyidiimide (50)


    Compound 50 is obtained by method 2. Yield: 23% (The proportion of each isomer cannot be determined). The reaction time for this compound was 72 hours. 1H NMR (300 MHz, CDCl3) į 0.85 (m, 6H), 1.30 (d, 44H), 1.44 (m, 4H), 1.70 (m, 4H), 3.24 (m , 4H), 7.02 (s, 2H), 7.50 (d, 2H), 7.60 (d, 2H), 8.75 5 (d, 2H), 8.85 (s, 2H), 8.95 (d, 2H). 13C NMR (CDCl3) į 22.38, 22.62, 22.68, 25.43, 28.44, 28.53, 29.35, 29.56, 25.69, 31.22, 31.70, 31.79, 31.92, 34.25, 35.58, 35.95, 47.18, 63.03, 69.34, 70.54, 121.99, 122.06, 122.42, 125, 87, 126.37, 127.63, 128.84, 129.10, 129.38, 129.82, 130.27, 130.89, 131.23, 132.63, 132.82, 133.15, 138.92, 143.86, 150.17, 164.46, 164.50. MALDI-TOF MS m / z,> M + @ theoretical C64H74N2O4S2
    10 998.51, experimental 988.55. IR (KBr): 2920, 2868, 1706, 1671, 1596, 1450, 1246, 802 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 434 (3.9), 567 (4.3).
    Example 51: N, N’-bis- (di-2 ’, 5’-t-butylphenyl) -1-hexylthioperylene-3,4: 9,10 tetracarboxidiimide (51)
    Compound 51 is obtained following method 1. Yield: 25%. 1H NMR (300 MHz, CDCl3) į 0.85 (m, 3H), 1.26 (s, 4H), 1.32-1.34 (d, 36H), 1.47 (m, 2H), 1 , 74 (m, 2H), 3.26 (m, 2H), 7.04 (s, 2H), 7.50 (d, 2H), 7.60 (d, 2H), 8.74 (s, 3H), 8.85 (m, 3H), 9.02 (d, 1H). 13C NMR (CDCl3) į 13.92, 22.38, 28.43, 28.54, 29.68, 31.21, 31.74,
    20 34.24, 35.54, 36.18, 36.24, 122.25, 122.65, 122.84, 123.24, 123.84, 136.34, 126.40, 126.77, 127 , 47, 127.62, 127.72, 128.19, 128.80, 129.24, 129.40, 130.16, 131.26, 131.95, 132.46, 132.66, 133.26 , 133.89, 134.53, 134.55, 134.75, 140.22, 143.78, 143.81, 150.16, 164.27, 164.40, 164.50, 164.70. MALDI-TOF MS m / z,> M + @ theoretical


    C58H62N2O4S 882.44, experimental 882.49. IR (KBr): 2967, 2926, 1706, 1677, 1584, 1403, 1339, 1257, 802, 750 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 447 (3.9), 546 (4.4).
    Example 52: N, N’-di- (1’-hexylheptyl) -2,5,8,11-tetrahexylthioperylene-3,4: 9,10 tetracarboxidiimide (52)
    Compound 52 is obtained following method 4. Yield: 90%. 1H NMR (300 MHz, CDCl3) į 0.83 (t, 12H), 0.93 (t, 12H), 1.30 (broad s, 52H), 1.65 (m, 4H), 1.94 ( m, 12H), 2.25 (m, 4H), 3.20 (t, 8H), 5.23 (m, 2H), 8.37 (s, 4H). 13C NMR (CDCl3) į 13.83,
    10 13.89, 13.90, 13.93, 22.34, 22.41, 22.46, 26.99, 27.79, 29.12, 31.42, 31.46, 31.59, 31 , 64, 32.11, 32.63, 54.81, 116.77, 117.93, 120.13, 124.01, 131.93, 150.47, 163.30, 164.04. MALDI-TOF MS m / z,> M + H + @ theoretical C74H110N2O4S4 1219.73, experimental 1219.77. IR (KBr): 2932, 2844, 1677, 1636, 1555, 1345, 1234, 849, 738 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 489 (5.1), 543 (5.1).
    Example 53: N, N’-di- (1’-hexylheptyl) -2-bromo-5,8,11-trihexylthioperylene-3,4: 9,10 tetracarboxyidiimide (53)


    Compound 53 is obtained following method 3. Yield: 66%. 1H NMR (300MHz, CDCl3) į 0.83 (t, 12H), 0.93 (t, 9H), 1.32 (broad s, 46H), 1.65 (m, 4H), 1.93 (m,5 10H), 2.22 (m, 4H), 3.17 (t, 6H), 5.20 (m, 2H), 8.13 (s, 1H), 8.22 (s, 1H), 8 , 30 (s, 1H),8.41 (s, 1 H). 13C NMR (CDCl3) į 14.02, 22.51, 22.59, 27.13, 27.20, 27.82, 28.07,29.14, 29.23, 29.25, 29.66, 31.57, 31.59, 31.60, 31.61, 31.64, 32.23, 32.54, 32.67,32.77, 32.85, 55.00, 55.39, 117.96, 118.53, 119.36, 119.67, 120.08, 122.13, 122.43,128.84, 128.95, 130.30, 131.30, 131.69, 132, 09, 132.19, 132.30, 132.80, 133.29,
    10 150.62, 151.15, 161.21, 163.29. MALDI-TOF MS m / z,> M + H + @ theoretical C68H97N2O4S3Br 1181.58 experimental 1181.61. IR (KBr): 2926, 2862, 1683, 1636, 1555, 1456, 1345, 1240, 814, 744 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 501 (4.7), 540 (4.8).
    Example 54: N, N’-di- (1’-hexylheptyl) -2,5-dibromo-8,11-dihexylthioperylene-3,4: 9,1015 tetracarboxyidiimide (54)


    Compound 54 is obtained following method 3. Yield: 25%. 1H NMR (300MHz, CDCl3) į 0.84 (t, 12H), 0.93 (t, 6H), 1.31 (broad s, 44H), 1.64 (m, 4H), 1.93 (m,4H), 2.21 (m, 4H), 3.19 (t, 4H), 5.19 (m, 2H), 8.43 (s, 2H), 8.54 (s, 2H). 13C NMR5 (CDCl3) į 13.83, 13.90, 13.91, 13.93, 22.34, 22.37, 22.39, 22.46, 23.46, 26.79, 26.93,27.73, 27.96, 28.16, 27.73, 27.96, 28.16, 28.74, 28.95, 29.08, 31.26, 31.43, 31.54,31.58, 31.62, 31.62, 32.08, 32.76, 55.32, 119.71, 122.19, 126.10, 129.57, 129.86,131.31, 131.62, 131.77, 131.95, 132.21, 133.00, 134.45, 151.28, 161.37, 163.29. EMMALDI-TOF m / z,> M + H + @ theoretical C62H84N2O4S2Br2 1143.42, experimental 1143.52. GO
    10 (KBr): 2958, 2917, 2855, 1695, 1646, 1229, 1025 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 487 (4.6), 540 (4.5).
    Example 55: N, N’-di- (1’-hexylheptyl) -1-butoxy-6 (7) -hexylthioperylene-3,4: 9,10 tetracarboxyidiimide (55)


    Compound 55 is obtained following method 5. Yield: 25%. 1H NMR (300
    MHz, CDCl3) į 0.83 (t, 15H), 1.07 (t, 3H), 1.24 (broad s, 38H), 1.66 (m, 4H), 1.87 (m,
    4H), 2.07 (m, 2H), 2.28 (m, 4H), 3.22, (m, 2H), 4.52 (m, 2H), 5.21 (m, 2H), 8 , 51 (s
    5 wide, 1H), 8.64 (wide s, 2H), 8.79 (m, 2H), 9.52 (1.6 isomer) 9.65 (1.7 isomer) (d, 1H). 13C NMR (CDCl3) į 13.83, 13.91, 14.02, 19.53, 19.57, 22.38, 22.57, 26.92, 28.39, 28.51, 29.22, 31.22, 31.39, 31.76, 32.42, 35.96, 36.47, 54.67, 70.24, 120.67, 121.96, 123.47, 123.87, 125, 65, 125.99, 128.21, 128.49, 128.57, 128.94, 129.22, 129.31, 129.50, 133.06, 133.30, 137.81, 138.53, 156.88, 157.24, 157.86, 163.79, 164.87. EM
    10 MALDI-TOF m / z,> M + @ theoretical C60H82N2O5S 942.59, experimental 942.64. IR (KBr): 2955, 2932, 2862, 1695, 1654, 1607, 1397, 1333, 1228, 808, 750 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 566 (4.8).
    Example 56: N, N’-di- (1’-hexylheptyl) -2-butoxy-5,8,11-trihexylthioperylene-3,4: 9,1015 tetracarboxyidiimide (56)


    Compound 56 is obtained following method 6. Yield: 28%. 1H NMR (300MHz, CDCl3) į 0.83 (t, 12H), 0.93 (t, 9H), 1.06 (t, 3H), 1.25 (broad s, 32H), 1.39 (swide, 14H), 1.64 (m, 4H), 1.94 (s wide, 12H), 2.04 (m, 2H), 2.24 (m, 4H), 3.20 (s5 wide, 6H), 4.45 (t, 2H), 5.24 (m, 2H), 8.07 (s, 1H), 8.34 (s, 1H), 8.36 (s, 1H) , 8.40 (s,1 HOUR). 13C NMR (CDCl3) į 13.86, 14.02, 14.05, 19.25, 22.53, 22.56, 22.58, 22.60, 27.07,27.92, 27.96, 29.23, 29.29, 29.69, 31.30, 31.56, 31.57, 31.76, 31.79, 31.92, 32.23,32.27, 32.58, 32.75, 54.91, 117.64, 118.11, 118.59, 120.21, 123.03, 123.22, 123.93,125.25, 129.72, 131.99, 132.08, 133.15, 161.55, 162.72, 163.54, 164.28. EM MALDI
    10 TOF m / z. > M + H + @ theoretical C72H106N2O5S3 1175.73, experimental 1175.75. IR (KBr): 2914, 2844, 1671, 1636, 1590, 1561, 1479, 1339, 1257, 802 cm-1. UV Vis (CH2Cl2), Omax / nm (log H): 473 (4.4), 501 (4.5), 540 (4.5).

    权利要求:
    Claims (23)
    [1]

    [ 1]
      1.- preparation procedure of the compounds of formula I:
    5 where: each R1 and R3 independently represent hydrogen, halogen, C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, -CN, -COR4, -CO2R4, -CONR4R4, -OR4, -OCOR4, -OCONR4R4, - OCO2R4, -SR4, -SeR4, -NR4R4, -NR4COR4, -NR4CONR4R4, -NR4CO2R4, –PR4R4, -SOR4, -SO2R4, -SO2NR4R4 or Cy1, where C1-C20 alkyl, C2-C20 alkenyl
    C2-C20 alkynyl are independently optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6; each R2 independently represents C1-C40 alkyl or Cy2; where C1-C40 alkyl is optionally substituted by one or more R5 and where Cy2 is optionally substituted by one or more R7;
    Each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20 alkyl is optionally substituted by one or more R10 and where Cy4 is optionally substituted by one or more R11;
    or two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that may additionally contain a selected heteroatom
    20 of N, O and S, and which may be optionally substituted by one or two R11; each R5 independently represents Cy3, -OR8, -SR8 or -NR8R8, where Cy3 is optionally substituted by one or more R6; each R7 independently represents C1-C40 alkyl, Cy4, -OR8, -SR8 or -NR8R8, where C1-C40 alkyl is optionally substituted by one or more R9 and where Cy4 is
    25 optionally substituted by one or more R6;

    each R8 independently represents hydrogen, C1-C6 alkyl or Cy3, where C1-C6 alkyl is optionally substituted by one or more -OH, -OC1-C4 alkyl, where C1-C4 alkyl is optionally substituted by one or more -OH and where Cy3 is optionally substituted by one or more C1-C6 alkyl;
    5 each R6 and R11 independently represent R8, -OR8, -SR8 or -NR8R8; each R9 and R10 independently represent -OR8, -SR8, -NR8R8 or Cy3, where Cy3 is optionally substituted by one or more C1-C6 alkyl; each Cy1 and Cy3 independently represent phenyl or a 5- or 6-membered aromatic heterocycle containing 1 to 3 heteroatoms selected from N, O, S and Se, and
    Where each Cy1 and Cy3 can be independently linked to the rest of the molecule through any available C or N atom; each Cy2 independently represents a saturated, partially unsaturated ring
    or aromatic, monocyclic of 3 to 7 members or bicyclic of 6 to 11 members that can be carbocyclic or heterocyclic, where Cy2 can be attached to the rest of the molecule a
    15 through any available C or N atom, where Cy2 contains 1 to 4 heteroatoms selected from N, O, S and Se, and where one or more C, S or Se atoms of Cy2 may optionally be oxidized to form CO groups , SO, SO2, SeO or SeO2; and each Cy4 independently represents a carbocyclic or heterocyclic ring
    20 saturated, partially unsaturated or aromatic 3 to 7 members, optionally containing 1 to 4 heteroatoms selected from N, O, S and Se, where Cy4 is attached to the rest of the molecule through any available C or N atom , and where one or more atoms of C, S or Se of Cy4 may optionally be oxidized forming groups CO, SO, SO2, SeO or SeO2,
    With the proviso that at least one R3 independently represents -OR4, -SR4, -SeR4, -NR4R4 or -PR4R4, which comprises reacting a compound of formula II with a compound of formula III in the presence of a fluorine source:

    R2
    R1
    R12 R12
    R1
    R13-H
    II III
    where:each R1 and R2 independently have the meaning described for a compound offormula I;
    5 each R12 independently represents hydrogen, halogen, -CN, -COR4, -CO2R4, -CONR4R4, -OR4, -OCOR4, -OCONR4R4, -OCO2R4, -SR4, -SeR4, -NR4R4, -NR4COR4,
    - NR4CONR4R4, -NR4CO2R4, -PR4R4, -SOR4, -SO2R4 or -SO2NR4R4;
    R13 represents –OR4, -SR4, -SeR4, -NR4R4 or -PR4R4; and each R4 independently has the meaning described for a compound of
    Formula I, with the proviso that at least one R12 independently represents hydrogen or halogen.
    [2]
    2. The method according to claim 1, wherein the fluorine source is selected from tetrabutylammonium fluoride (TBAF), tetraphenylphosphonium fluoride (TPPF), CsF, RbF, KF, NaF, LiF, BaF2, SrF2, CaF2, and MgF2
    [3]
     3. The process according to claim 2, wherein the fluorine source is selected from tetrabutylammonium fluoride (TBAF) and KF.
    The method according to any one of claims 1 to 3, wherein each R1 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, -SeR4, -NR4R4, -PR4R4 or Cy1, wherein C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.

    [5]
    5. The process according to any of claims 1 to 4, wherein each R2 independently represents C1-C40 alkyl optionally substituted by one or more R5.
    The method according to any of claims 1 to 4, wherein each R2independently represents Cy2 optionally substituted by one or more R7.
    [7]
    7. The method according to any of claims 1 to 6, wherein each R3 independently represents hydrogen, halogen, C1-C20 alkyl, -OR4, -SR4, 10 -SeR4, -NR4R4, -PR4R4 or Cy1, wherein C1-C20 alkyl is optionally substituted by one or more R5 and Cy1 is optionally substituted by one or more R6.
    [8]
    8. The method according to any one of claims 1 to 7, wherein each R4 independently represents hydrogen, C1-C20 alkyl or Cy4, where C1-C20 alkyl 15 is optionally substituted by one or more R10 and where Cy4 is optionally substituted by one or more R11.
    [9]
    9. The method according to any of claims 1 to 7, wherein each R4 independently represents C1-C20 alkyl optionally substituted by one or more R10.
    [10]
    10. The method according to any one of claims 1 to 7, wherein two R4 groups can be joined by forming with the N atom a saturated 5- to 7-membered heterocycle that additionally can contain a selected heteroatom
    25 of N, O and S, and which may be optionally substituted by one or two R11.
    [11]
     11. The method according to any of claims 1 to 10, wherein each R6 independently represents R8.
    12. The method according to any of claims 1 to 11, wherein each R7 independently represents C1-C40 alkyl optionally substituted by one or more R9.
    [13]
    13. The process according to any of claims 1 to 12, wherein each R8 independently represents C1-C6 alkyl optionally substituted by one or more

    - OH, -OC1-C4 alkyl and where C1-C4 alkyl is optionally substituted by one or more -OH.
    [14]
    14. The method according to any of claims 1 to 13, wherein each R9 independently represents -OR8 or Cy3, wherein Cy3 is optionally substituted by one or more C1-C6 alkyl.
    [15]
    15. The method according to any of claims 1 to 14, wherein each R10 independently represents -OR8 or Cy3, wherein Cy3 is optionally substituted by one or more C1-C6 alkyl.
    [16]
    16. The method according to any of claims 1 to 15, wherein each R11 independently represents R8.
    [17]
    17. The process according to any of claims 1 to 16, wherein each Cy1 independently represents phenyl.
    [18]
     18. The method according to any of claims 1 to 16, wherein each Cy1 independently represents:
    ;
    ;
    or
    .
    [19]
     19. The process according to any of claims 1 to 18, wherein each Cy2 independently represents phenyl.
    [20]
    20. The method according to any of claims 1 to 18, wherein each Cy2 independently represents a saturated, monocyclic ring of 3 to 7 heterocyclic members, where Cy2 can be attached to the rest of the molecule through any C or N atom available, and where Cy2 contains 1 to 3 heteroatoms selected from N, O and S.
    [21]
     21. The process according to any of claims 1 to 20, wherein each Cy3 independently represents phenyl.

    [22]
    22. The method according to any of claims 1 to 20, wherein each Cy3 independently represents a 5 or 6-membered aromatic heterocycle containing 1 or 2 heteroatoms selected from N, O and S, and where Cy3 can be attached to the rest of the molecule through any available C or N atom.
    523.- The method according to any of claims 1 to 22, wherein each Cy4independently represents a saturated heterocyclic ring, 3 to 7 members,which optionally contains 1 to 3 heteroatoms selected from N, O and S, andwhere Cy4 is attached to the rest of the molecule through any C or N atom
    10 available.
    [24]
     24. The process according to any of claims 1 to 22, wherein each Cy4 independently represents phenyl.
    The method according to any one of claims 1 to 24, wherein each R12 independently represents hydrogen, halogen, -OR4, -SR4, -SeR4, -NR4R4 or -PR4R4.
    [26]
    26.- A compound selected from:
    24 25
     twenty , , .

    , Y
    [27]
    27.- Use of a compound according to claim 26, for the preparation of dyes, pigments, paints, fluorescent agents, optical devices, electronic devices, electro-optical devices, light emitting diodes and organic or hybrid photovoltaic cells.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US4845223A|1985-12-19|1989-07-04|Basf Aktiengesellschaft|Fluorescent aryloxy-substituted perylene-3,4,9,10-tetracarboxylic acid diimides|
    WO2008139452A2|2007-05-09|2008-11-20|Yeda Research And Development Co.Ltd|Selective bromination of perylene diimides and derivatives thereof under mild conditions|
    US9865819B2|2016-06-06|2018-01-09|Uti Limited Partnership|Nitrogen annulated perylene diimides for use as electron transport materials in organic electronic devices|
    US10647732B2|2018-01-09|2020-05-12|Uti Limited Partnership|N-annulated perylene diimide dimers with active pyrrolic N—H bonds|
    WO2020100783A1|2018-11-13|2020-05-22|住友化学株式会社|Coloring composition|
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