Amphiphilic and mesogenic organic dyes for tailor-made reflective low-dimensional materials

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, COR11, CO2R12, CONR13R14, SO2R15, CN or NO2, 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 hydrogen atom, a halogen atom, a (C1-C20)alkyl, (C1-C20)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, cycloalkyl, 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-C20)alkyl, (C1-C20)haloalkyl, cycloalkyl, heterocycle or O(C1-C20)alkyl group;
• R1 represents a halogen atom, a (C1-C20)alkyl, (C2-C12)alkynyl, (C1-C20)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, COR32, OCOR36 or NR38COR39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• R4 represents a halogen atom, a (C1-C20)alkyl, (C2-C12)alkynyl, (C1-C20)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, COR32, OCOR36 or NR38COR39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• or
• both R4 groups form together a bond or a chain selected from the group consisting of —C(R42R43)—, —(CH2)n—, —Si(R44R45)—, —CH2—Y—CH2—, and -Y—CH2—CH2—Y′—, wherein:
• Y and Y′ each represent, independently of each other, O, S or NH,
• n is equal to 2 or 3,
• R42 and R43, each represent, independently of each other, a (C1-C6)alkyl or an aryl group, and
• R44 and R45 each represent, independently of each other, a (C1-C6)alkyl or an aryl group;
• L represents a bond, or a group selected from the group consisting of:
• R2 and R3 each represent, independently of each other, a hydrogen atom, 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, OR49 or NR51R52 group;
• or
• L represents:
• and
• Rf and R2, and Rg and R3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• RN and RN′ each represent, independently of each other, a (C7-C20)alkyl or (C7-C20)haloalkyl group, said group being optionally substituted by one or more groups selected from OR62, SR63 and NR64R65, or a group selected from the group consisting of:
• wherein:
• X represents O, S or NR57,
• Y represents OR58, SR59 or NR60 R61,
• x is equal to 0, 1, 2 or 3,
• y is equal to 0, 1, 2 or 3,
• z is equal to 0, 1, 2 or 3,
• Rk and R1 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group,
• Rm represents a (C1-C20)alkyl group,
• Rr represents a hydrogen atom or a (C1-C6)alkyl group,
• Rp and Rq each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl, an aryl or heteroaryl group,
• R57 to R65 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• R5 to R8, R11 to R15, R24, R25, R28, R29, R32, R36, R38, R39, R49, R51 and R52 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, OR64, SR65 and NR66R67 group, wherein R64 to R67 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• R22, R23, R26 and R27 each represent, independently of each other a hydrogen atom, a (C1-C20)alkyl, (C1-C20)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, OR66, SR67 and NR68R69 group, wherein R66 to R69 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• A− represents a monovalent, organic or inorganic anion,
• with the proviso that when R1 and R4 are the same, and R0 is:
• wherein Z represents C,
• at least one of Ra and Re is not the same as R1.

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, COR11, CO2R12, CONR13R14, SO2R15, CN or NO2, 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 hydrogen atom, a halogen atom, a (C1-C20)alkyl, (C1-C20)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, cycloalkyl, 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-C20)alkyl, (C1-C20)haloalkyl, cycloalkyl, heterocycle or O(C1-C20)alkyl group;
• R1 represents a halogen atom, a (C1-C20)alkyl, (C2-C12)alkynyl, (C1-C20)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, heteroaryl-(C1-C6)alkyl, cycloalkyl, cycloalkyl-(C1-C6)alkyl, heterocycle, heterocycle-(C 1-C6)alkyl, (CH2)mOR24, (CH2)m′SR25, OR26, SR27, NR28R29, COR32, OCOR36 or NR38COR39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• R4 represents a halogen atom, a (C1-C20)alkyl, (C2-C12)alkynyl, (C1-C20)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, COR32, OCOR36 or NR38COR39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• or
• both R4 groups form together a bond or a chain selected from the group consisting of —C(R42R43)—, —(CH2)n—, —Si(R44R45)—, —CH2—Y—CH2—, and -Y—CH2—CH2—Y′—, wherein:
• Y and Y′ each represent, independently of each other, O, S or NH,
• n is equal to 2 or 3,
• R42 and R43, each represent, independently of each other, a (C1-C6)alkyl or an aryl group, and
• R44 and R45 each represent, independently of each other, a (C1-C6)alkyl or an aryl group;
• L represents a bond, or a group selected from the group consisting of:
• R2 and R3 each represent, independently of each other, a hydrogen atom, 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, OR49 or NR51R52 group;
• or
• L represents:
• and
• Rf and R2, and Rg and R3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• RN and RN′ each represent, independently of each other, a (C7-C20)alkyl or (C7-C20)haloalkyl group, said group being optionally substituted by one or more groups selected from OR62, SR63 and NR64R65, or a group selected from the group consisting of:
• wherein:
• X represents O, S or NR57,
• Y represents OR58, SR59 or NR60 R61,
• x is equal to 0, 1, 2 or 3,
• y is equal to 0, 1, 2 or 3,
• z is equal to 0, 1, 2 or 3,
• Rk and R1 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group,
• Rm represents a (C1-C20)alkyl group,
• Rr represents a hydrogen atom or a (C1-C6)alkyl group,
• Rp and Rq each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl, an aryl or heteroaryl group,
• R57 to R65 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• R5 to R8, R11 to R15, R24, R25, R28, R29, R32, R36, R38, R39, R49, R51 and R52 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, OR64, SR65 and NR66R67 group, wherein R64 to R67 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• R22, R23, R26 and R27 each represent, independently of each other a hydrogen atom, a (C1-C20)alkyl, (C1-C20)haloalkyl, aryl, heteroaryl, aryl-(C 1-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, OR66, SR67 and NR68R69 group, wherein R66 to R69 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• A− represents a monovalent, organic or inorganic anion, with the proviso that when R1 and R4 are the same, and R0 is:
• wherein Z represents C,
• at least one of Ra and Re is not the same as R1.

A chromophore comprising 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, COR11, CO2R12, CONR13R14, SO2R15, CN or NO2, 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 hydrogen atom, a halogen atom, a (C1-C20)alkyl, (C1-C20)haloalkyl, aryl, heteroaryl, aryl-(C1-C6)alkyl, cycloalkyl, 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-C20)alkyl, (C1-C20)haloalkyl, cycloalkyl, heterocycle or O(C1-C20)alkyl group;
• R1 represents a halogen atom, a (C1-C20)alkyl, (C2-C12)alkynyl, (C1-C20)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, COR32, OCOR36 or NR38COR39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• R4 represents a halogen atom, a (C1-C20)alkyl, (C2-C12)alkynyl, (C1-C20)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′SR25,0R26, SR27, NR28R29, COR32, OCOR36 or NR38COR39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;
• or
• both R4 groups form together a bond or a chain selected from the group consisting of —C(R42R43)—, —(CH2)n—, —Si(R44R45)— and —Y—CH2—CH2—Y′—, wherein:
• Y and Y′ each represent, independently of each other, O, S or NH,
• n is equal to 2 or 3,
• R42 and R43, each represent, independently of each other, a (C1-C6)alkyl or an aryl group, and
• R44 and R45 each represent, independently of each other, a (C1-C6)alkyl or an aryl group;
• L represents a bond, or a group selected from the group consisting of:
• R2 and R3 each represent, independently of each other, a hydrogen atom, 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, OR49 or NR51R52 group;
• or
• L represents:
• and
• Rf and R2, and Rg and R3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;
• RN and RN′ each represent, independently of each other, a (C7-C20)alkyl or (C7-C20)haloalkyl group, said group being optionally substituted by one or more groups selected from OR62, SR63 and NR64R65, or a group selected from the group consisting of:
• wherein:
• X represents O, S or NR57,
• Y represents OR58, SR59 or NR60 R61,
• x is equal to 0, 1, 2 or 3,
• y is equal to 0, 1, 2 or 3,
• z is equal to 0, 1, 2 or 3,
• Rk and R1 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group,
• Rm represents a (C1-C20)alkyl group,
• Rr represents a hydrogen atom or a (C1-C6)alkyl group,
• Rp and Rq each represent, independently of each other, a hydrogen atom, a (C1-C6)alkyl, an aryl or heteroaryl group,
• R57 to R65 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• R5 to R8, R11 to R15, R24, R25, R28, R29, R32, R36, R38, R39, R49, R51 and R52 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, OR64, SR65 and NR66R67 group, wherein R64 to R67 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• R22, R23, R26 and R27 each represent, independently of each other a hydrogen atom, a (C1-C20)alkyl, (C1-C20)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, OR66, SR67 and NR68R69 group, wherein R66 to R69 each represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group;
• and
• A− represents a monovalent, organic or inorganic anion,
• with the proviso that when R1 and R4 are the same, and R0 is:
• wherein Z represents C,
• at least one of Ra and Re is not the same as R1.