Organic Materials with Special Optical Effects

A supramolecular material, comprising a self-assembly of a compound of following general formula (I):

• wherein:
• R0 represents a hydrogen atom, a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, OR5, SR6, NR7R8, PR9R10, COR11, CO2R12, CONR13R14, SO2R15, SO3H, CN, NO2, OCOR16, OCO2R17, NR18COR19 or NR20SO2R21 group, or is selected from the group consisting of:
• wherein:
• Z represents C or N+ Az− and Z′ represents N or N+—Rc′ Az−, wherein
• Az− represents a monovalent organic or inorganic anion, and
• Rc′ represents a hydrogen atom or a (C1-C6)alkyl group,
• Ra and Re each represent, independently of each other, a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, OR22 or SR23 group, and
• Rb, Rc and Rd each represent, independently of each other, a hydrogen atom, a halogen atom or a (C1-C6)alkyl, (C1-C6)haloalkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle or heterocycle-(C1-C6)alkyl group;
• R1═R1′, and R1 represents a halogen atom, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, (CH2)mOR24, (CH2)m′SR25, OR26, SR27, NR28R29, PR30R31, COR32, CO2R33, CONR34R35, OCOR36, OCO2R37, NR38COR39, or NR40SO2R41 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• R4═R4′, and R4 represents a halogen atom, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, (CH2)mOR24, (CH2)m′SR25, OR26, SR27, NR28R29, PR30R31, COR32, CO2R33, CONR34R35, OCOR36, OCO2R37, NR38COR39, or NR40SO2R41 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• with the proviso that when R1 and R4 are the same, at least one of Ra and Re is not the same as R1;
• or
• R4 and R4′ form together a bond or a chain selected from the group consisting of —C(R74R75)—, —(CH2)n—, —Si(R76R77)—, —(CH2)p—Y—(CH2)q—, and —Y—(CR78R79)r—Y′—, wherein:
• Y and Y′ each represent, independently of each other, O, S or NR80,
• n is equal to 2 or 3,
• p is equal to 1 or 2,
• q is equal to 0 or 1,
• r is equal to 1 or 2,
• R74, R75, R78 to R80 each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl or an aryl group, and
• R76 and R77 each represent, independently of each other, a (C1-C6)alkyl or an aryl group;
• R2═R2′, R3═R3′, and R2 and R3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, OR42, SR43, NR44R45, COR46, CO2R47 or CONR48R49 group;
• LX=LX′, and LX represents a bond, or a group selected from the group consisting of:
• wherein Rf, Rg and Rh each represent, independently of each other, a hydrogen or halogen atom, a (C1-C6)alkyl or (C1-C6)haloalkyl group;
• X═X′, and X represents NR50R51, PR52R53, OR54, SR55, heterocycle, heteroaryl or aryl, wherein:
• said heterocycle and heteroaryl group comprise at least one heteroatom bearing a lone pair of electrons conjugated with C+, and are optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR56, SR57 and NR58R59, and
• said aryl is para-substituted by a group selected from NR60R61, PR62R63, OR64 and SR65, and optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR66, SR67 and NR68R69;
• or
• R1 together with R2, and R1′ together with R2′ form together with the carbon atoms that carry them an identical cycle selected from the group consisting of cycloalkenyl, heterocycle, aryl and heteroaryl, said cycle being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR70, SR71 and NR72R73;
• and/or
• R3 together with R4, and R3′ together with R4′ form together with the carbon atoms that carry them an identical cycle selected from the group consisting of cycloalkenyl, heterocycle, aryl and heteroaryl, said cycle being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR70, SR71 and NR72R73;
• and/or
• LX=LX′ and LX represents a bond;
• X═X′ and X represents NR50′R51′, PR52′R53′, OR54′ or SR55′;
• and
• R2 and NR50′, and R2′ and NR50′;
• R2 and PR2′, and R2′ and PR2′;
• R2 and OR54′, and R2′ and OR54′;
• or R2 and SR55′, and R2′ and SR55′ form together with the carbon atoms that carry them a heterocycle or heteroaryl group, said group being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR81, SR82 and NR83R84;
• and/or
• R3 and NR51′, and R3′ and NR51′;
• R3 and PR53′, and R3′ and PR53′;
• R3 and OR54′, and R3′ and OR54′;
• or R3 and SR55′, and R3′ and SR55′ form together with the carbon atoms that carry them a heterocycle or heteroaryl group, said group being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR81, SR82 and NR83R84;
• and R50′, R51′, R52′ and R53′ represent respectively R50, R51, R52 and R53 when they are not linked with R2 or R3;
• and/or
• LX=LX′ and Lx represents
• and R2 and Rf′, and R2′ and Rf′;
• or R2 and Rg′ and R2′ and Rg′ form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• and/or
• R3 and Rg′, and R3′ and Rg′ form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• and Rf′, Rg′ and Rh′ represent respectively Rf, Rg and Rh when they are not linked with R2 or R3;
• and
• R5 to R53, R56 to R63, R66 to R73 and R81 to R84 each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle or heterocycle-(C1-C6)alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, OR85, SR86 and NR87R88 group, wherein R85 to R88 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• R54, R55, R64 and R65 each represent, independently of each other, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle or heterocycle-(C1-C6)alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, OR85, SR86 and NR87R88 group, wherein R85 to R88 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• A− represents a monovalent or multivalent, organic or inorganic anion.

A reflective or photonic or nanophotonic or optoelectronic device, comprising at least one compound of following general formula (I):

• wherein:
• R0 represents a hydrogen atom, a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, OR5, SR6, NR7R8, PR9R10, COR11, CO2R12, CONR13R14, SO2R15, SO3H, CN, NO2, OCOR16, OCO2R17, NR18COR19 or NR20SO2R21 group, or is selected from the group consisting of:
• wherein:
• Z represents C or N+ Az− and Z′ represents N or N+—Rc′ Az−, wherein
• Az− represents a monovalent organic or inorganic anion, and
• Rc′ represents a hydrogen atom or a (C1-C6)alkyl group,
• Ra and Re each represent, independently of each other, a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, OR22 or SR23 group, and
• Rb, Rc and Rd each represent, independently of each other, a hydrogen atom, a halogen atom or a (C1-C6)alkyl, (C1-C6)haloalkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle or heterocycle-(C1-C6)alkyl group;
• R1═R1′, and R1 represents a halogen atom, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, (CH2)mOR24, (CH2)m′SR25, OR26, SR27, NR28R29, PR30R31, COR32, CO2R33, CONR34R35, OCOR36, OCO2R37, NR38COR39, or NR40SO2R41 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• R4═R4′, and R4 represents a halogen atom, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, (CH2)mOR24, (CH2)m′SR25, OR26, SR27, NR28R29, PR30R31, COR32, CO2R33, CONR34R35, OCOR36, OCO2R37, NR38COR39, or NR40SO2R41 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• with the proviso that when R1 and R4 are the same, at least one of Ra and Re is not the same as R1;
• or
• R4 and R4′ form together a bond or a chain selected from the group consisting of —C(R74R75)—, —(CH2)n—, —Si(R76R77)—, —(CH2)p—Y—(CH2)q—, and —Y—(CR78R79)r—Y′—, wherein:
• Y and Y′ each represent, independently of each other, O, S or NR80,
• n is equal to 2 or 3,
• p is equal to 1 or 2,
• q is equal to 0 or 1,
• r is equal to 1 or 2,
• R74, R75, R78 to R80 each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl or an aryl group, and
• R76 and R77 each represent, independently of each other, a (C1-C6)alkyl or an aryl group;
• R2═R2′, R3═R3′, and R2 and R3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C1-C6)alkyl, OR42, SR43, NR44R45, COR46, CO2R47 or CONR48R49 group;
• LX=LX′, and LX represents a bond, or a group selected from the group consisting of:
• wherein Rf, Rg and Rh each represent, independently of each other, a hydrogen or halogen atom, a (C1-C6)alkyl or (C1-C6)haloalkyl group;
• X═X′, and X represents NR50R51, PR52R53, OR54, SR55, heterocycle, heteroaryl or aryl, wherein:
• said heterocycle and heteroaryl group comprise at least one heteroatom bearing a lone pair of electrons conjugated with C+, and are optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR56, SR57 and NR58R59, and
• said aryl is para-substituted by a group selected from NR60R61, PR62R63, OR64 and SR65, and optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR66, SR67 and NR68R69;
• or
• R1 together with R2, and R1′ together with R2′ form together with the carbon atoms that carry them an identical cycle selected from the group consisting of cycloalkenyl, heterocycle, aryl and heteroaryl, said cycle being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR70, SR71 and NR72R73;
• and/or
• R3 together with R4, and R3′ together with R4′ form together with the carbon atoms that carry them an identical cycle selected from the group consisting of cycloalkenyl, heterocycle, aryl and heteroaryl, said cycle being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR70, SR71 and NR72R73;
• and/or
• LX=LX′ and LX represents a bond;
• X═X′ and X represents NR50′R51′, PR2′R53′, OR54′ or SR55′;
• and
• R2 and NR50′, and R2′ and NR50′;
• R2 and PR52′, and R2′ and PR2′;
• R2 and OR54′, and R2′ and OR54′;
• or R2 and SR55′, and R2′ and SR55′ form together with the carbon atoms that carry them a heterocycle or heteroaryl group, said group being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR81, SR82 and NR83R84;
• and/or
• R3 and NR51′, and R3′ and NR51′;
• R3 and PR53′, and R3′ and PR53′;
• R3 and OR54′, and R3′ and OR54′;
• or R3 and SR55′, and R3′ and SR55′ form together with the carbon atoms that carry them a heterocycle or heteroaryl group, said group being optionally substituted by one or more groups selected from a halogen atom, (C1-C6)alkyl, (C1-C6)haloalkyl, OR81, SR82 and NR83R84;
• and R50′, R51′, R52′ and R53′ represent respectively R50, R51, R52 and R53 when they are not linked with R2 or R3;
• and/or
• LX=LX′ and Lx represents
• and R2 and Rf′, and R2′ and Rf′;
• or R2 and Rg′ and R2′ and Rg′ form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• and/or
• R3 and Rg′, and R3′ and Rg′ form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• and Rf′, Rg′ and Rh′ represent respectively Rf, Rg and Rh when they are not linked with R2 or R3;
• and
• R5 to R53, R56 to R63, R66 to R73 and R81 to R84 each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle or heterocycle-(C1-C6)alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, OR85, SR86 and NR87R88 group, wherein R85 to R88 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• R54, R55, R64 and R65 each represent, independently of each other, a (C1-C6)alkyl, (C1-C6)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle or heterocycle-(C1-C6)alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C1-C6)alkyl, (C1-C6)haloalkyl, OR85, SR86 and NR87R88 group, wherein R85 to R88 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• A− represents a monovalent or multivalent, organic or inorganic anion.