IP Library › Granted Patent US 11,407,743

Granted Patent B2

US 11,407,743 · App. 17/257,031 · Granted Aug 9, 2022

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

Inventors: Philippe Laine (Paris, FR); Laurélie Poulard (Aulnay-sous-Bois, FR); Grégory Dupeyre (La Queue en Brie, FR); Valerie Marvaud (Paris, FR)

Assignees: Sorbonne Universite; Centre National De La Recherche Scientifique; Universite de Paris

C07D409/12 C07C211/50 C07C217/84 C07C217/94 C07D321/00 C07F7/0816 C09B11/12 C09B11/26 C09D5/004 C09D7/41 C07C2603/18 C07C2603/24 C07C2603/32

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Quick Facts

Patent No.: US 11,407,743
App. No.: 17/257,031
Granted: Aug 9, 2022
Kind: B2

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Abstract

The present invention relates to a compound of the following formula (I): The invention also relates to uses thereof as dye or pigment, notably as a luster pigment. The invention relates also to a reflective or photonic or nanophotonic or optoelectronic device comprising a compound of the invention. The invention relates also to a metal-like reflective coating, a metal-like particle or an organic-based metal-like liquid film comprising a compound of the invention.

Claims (203)

1. A compound of following general formula (I):

wherein:

R 0 represents a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 5 , SR 6 , NR 7 R 8 , COR 11 , CO 2 R 12 , CONR 13 R 14 , SO 2 R 15 , CN or NO 2 , group, or is selected from the group consisting of:

wherein:

Z represents C or N + A z − and Z′ represents N or N + —R c ′ A z − , wherein

A z − represents a monovalent organic or inorganic anion, and

R c ′ represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R a and R e each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 22 or SR 23 group, and

R b , R c and R d each represent, independently of each other, a hydrogen atom, a halogen atom or a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, cycloalkyl, heterocycle or O(C 1 -C 20 )alkyl, group;

R 1 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 )m′SR 25 , OR 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

R 4 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 )m′SR 25,0 R 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

both R 4 groups form together a bond or a chain selected from the group consisting of —C(R 42 R 43 )—, —(CH 2 ) n —, —Si(R 44 R 45 )—,—CH 2 —Y—CH 2 —, and —Y—CH 2 —CH 2 —Y′—, wherein:

Y and Y′ each represent, independently of each other, O, S or NH,

n is equal to 2 or 3,

R 42 and R 43 , each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group, and

R 44 and R 45 each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group;

L represents a bond, or a group selected from the group consisting of:

R 2 and R 3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C6)alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 49 or NR 51 R 52 group;

L represents:

and

R f and R 2 , and R g and R 3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;

R N and R N ′ each represent, independently of each other, a (C 7 -C 20 )alkyl or (C 7 -C 20 )haloalkyl group, said group being optionally substituted by one or more groups selected from OR 62 , SR 63 and NR 64 R 65 , or a group selected from the group consisting of:

wherein:

X represents O, S or NR 57 ,

Y represents OR 58 , SR 59 or NR 60 R 61 ,

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,

R k and R l each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group,

R m represents a (C 1 -C 20 )alkyl group,

R r represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R p and R q each represent, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, an aryl or heteroaryl group,

R 57 to R 65 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

R 5 to R 8 , R 11 to R 15 , R 24 , R 25 , R 28 , R 29 , R 32 , R 36 , R 38 , R 39 , R 49 , R 51 and R 52 each represent, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle or heterocycle-(C 1 -C 6 )alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 64 , SR 65 and NR 66 R 67 group, wherein R 64 to R 67 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

R 22 , R 23 , R 26 and R 27 each represent, independently of each other a hydrogen atom, a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle or heterocycle-(C 1 -C 6 )alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 66 , SR 67 and NR 68 R 69 group, wherein R 66 to R 69 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

and

A − represents a monovalent, organic or inorganic anion,

with the proviso that when R 1 and R 4 are the same, and R 0 is:

wherein Z represents C,

at least one of R a and R e is not the same as R 1 .

2. The compound according to claim 1 , wherein R N =R N ′.

3. The compound according to claim 1 , wherein R 0 represents a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, cycloalkyl, heterocycle, OR 5 , SR 6 , NR 7 R 8 , CN, or NO 2 group, or is selected from the group consisting of:

wherein:

Z represents C or N + A z − and Z′ represents N or N + —R c ′ A z − , wherein

A z − represents a monovalent organic or inorganic anion, and

R c ′ represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R a and R e each represent, independently of each other, hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 22 or SR 23 group, and

R b , R c and R d each represent, independently of each other, a hydrogen atom, a halogen atom or a (C 1 -C 6 )alkyl or (C 1 -C 6 )haloalkyl group,

with the proviso that when R 1 and R 4 are the same, and R 0 is:

wherein Z represents C,

at least one of R a and R e is not the same as R 1 .

4. The compound according to claim 1 , wherein R 0 represents a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, CN or NO 2 group, or is:

wherein:

Z represents C,

R a and R e each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl or (C 1 -C 6 )haloalkyl group, and

R b , R c and R d each represent a hydrogen atom.

5. The compound according to claim 1 , wherein R 1 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 , OR 26 , SR 27 or NR 28 R 29 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3.

6. The compound according to claim 1 , wherein:

R 4 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 , OR 26 , SR 27 or NR 28 R 29 group wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

both R 4 groups form together a bond or a chain selected from the group consisting of —C(R 42 R 43 )—, —(CH 2 ) n —, —Si(R 44 R 45 )—and —Y—CH 2 —CH 2 —Y′—, wherein:

Y and Y′ each represent, independently of each other, O, S or NH,

n is equal to 2 or 3,

R 42 and R 43 , each represent, independently of each other, a (C 1 -C 6 )alkyl group, and

R 44 and R 45 each represent, independently of each other, a (C 1 -C 6 )alkyl group.

7. The compound according to claim 1 , wherein L represents a bond.

8. The compound according to claim 1 , wherein R 2 and R 3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl or (C 1 -C 6 )haloalkyl group, notably a hydrogen atom or a (C 1 -C 6 )alkyl group.

9. The compound according to claim 1 , wherein R 1 =R 4 and/or R 2 =R 3 and/or R a =R e .

10. The compound according to claim 1 , wherein it is chosen from the following compounds:

11. The compound according to claim 1 , wherein A − represents a hexafluorophosphate, tetrafluoroborate, tetraphenylborate, 2,3-dichloro-5,6-dicyano-4-hydroxyphenolate (DDQH − ), halide or triflate anion.

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

wherein:

Z represents C or N + A z − and Z′ represents N or N + —R c ′ A z − , wherein

A z − represents a monovalent organic or inorganic anion, and

R c ′ represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R a and R e each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, cycloalkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 22 or SR 23 group, and

R b , R c and R d each represent, independently of each other, a hydrogen atom, a halogen atom or a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, cycloalkyl, heterocycle or O(C 1 -C 20 )alkyl group;

R 1 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 , OR 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

R 4 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 ,OR 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

both R 4 groups form together a bond or a chain selected from the group consisting of —C(R 42 R 43 )—, —(CH 2 ) n —, —Si(R 44 R 45 )—, —CH 2 —Y—CH 2 —, and -Y—CH 2 —CH 2 —Y′—, wherein:

Y and Y′ each represent, independently of each other, O, S or NH,

n is equal to 2 or 3,

R 42 and R 43 , each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group, and

R 44 and R 45 each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group;

L represents a bond, or a group selected from the group consisting of:

R 2 and R 3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 49 or NR 51 R 52 group;

L represents:

and

R f and R 2 , and R g and R 3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;

wherein:

X represents O, S or NR 57 ,

Y represents OR 58 , SR 59 or NR 60 R 61 ,

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,

R k and R 1 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group,

R m represents a (C 1 -C 20 )alkyl group,

R r represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R p and R q each represent, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, an aryl or heteroaryl group,

R 57 to R 65 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

and

A − represents a monovalent, organic or inorganic anion,

with the proviso that when R 1 and R 4 are the same, and R 0 is:

wherein Z represents C,

at least one of R a and R e is not the same as R 1 .

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

wherein:

Z represents C or N + A z − and Z′ represents N or N + —R c ′ A z − , wherein

A z − represents a monovalent organic or inorganic anion, and

R c ′ represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R b , R c and R d each represent, independently of each other, a hydrogen atom, a halogen atom or a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, cycloalkyl, heterocycle or O(C 1 -C 20 )alkyl group;

R 1 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 , OR 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

R 4 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 ,OR 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

Y and Y′ each represent, independently of each other, O, S or NH,

n is equal to 2 or 3,

R 42 and R 43 , each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group, and

R 44 and R 45 each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group;

L represents a bond, or a group selected from the group consisting of:

R 2 and R 3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 49 or NR 51 R 52 group;

L represents:

and

R f and R 2 , and R g and R 3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;

wherein:

X represents O, S or NR 57 ,

Y represents OR 58 , SR 59 or NR 60 R 61 ,

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,

R k and R 1 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group,

R m represents a (C 1 -C 20 )alkyl group,

R r represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R p and R q each represent, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, an aryl or heteroaryl group,

R 57 to R 65 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

R 5 to R 8 , R 11 to R 15 , R 24 , R 25 , R 28 , R 29 , R 32 , R 36 , R 38 , R 39 , R 49 , R 51 and R 52 each represent, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle or heterocycle-(C 1 -C 6 )alkyl group, said group being optionally substituted by one or more groups selected from a halogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 64 , SR 65 and NR 66 R 67 group, wherein R64 to R67 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

A − represents a monovalent, organic or inorganic anion, with the proviso that when R 1 and R 4 are the same, and R 0 is:

wherein Z represents C,

at least one of R a and R e is not the same as R 1 .

14. The supramolecular material according to claim 12 , wherein the supramolecular material is an organic-based metal-like liquid film (OMELLF).

15. The supramolecular material according to claim 12 , wherein the supramolecular material is a metal-like reflective coating or a metal-like particle.

16. The compound according to claim 1 , wherein R 22 , R 23 , R 26 and R 27 each represent, independently of each other a hydrogen atom or a (C 1 -C 20 )alkyl, (C 1 -C 12 )alkyl or a (C 1 -C 6 )alkyl group.

17. The compound according to claim 1 , wherein R 5 to R 8 , R 11 to R 15 , R 24 , R 25 , R 28 , R 29 , R 32 , R 36 , R 38 , R 39 , R 49 ; R 51 and R 52 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group.

18. The compound according to claim 1 , wherein R 0 represents a hydrogen atom, a (C 1 -C 6 )alkyl or a CN group, notably a hydrogen atom or a CN group.

19. The compound according to claim 1 , wherein R 2 and R 3 both represent a hydrogen atom.

20. The supramolecular material according to claim 12 , wherein the supramolecular material is a pigment.

21. A chromophore comprising a compound of following general formula (I):

wherein:

Z represents C or N + A z − and Z′ represents N or N + —R c ′ A z − , wherein

A z − represents a monovalent organic or inorganic anion, and

R c ′ represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R b , R c and R d each represent, independently of each other, a hydrogen atom, a halogen atom or a (C 1 -C 20 )alkyl, (C 1 -C 20 )haloalkyl, cycloalkyl, heterocycle or O(C 1 -C 20 )alkyl group;

R 1 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25 , OR 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

R 4 represents a halogen atom, a (C 1 -C 20 )alkyl, (C 2 -C 12 )alkynyl, (C 1 -C 20 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, (CH 2 ) m OR 24 , (CH 2 ) m ′SR 25,0 R 26 , SR 27 , NR 28 R 29 , COR 32 , OCOR 36 or NR 38 COR 39 group, wherein m and m′ are, independently of each other, equal to 1, 2 or 3;

both R 4 groups form together a bond or a chain selected from the group consisting of —C(R 42 R 43 )—, —(CH 2 ) n —, —Si(R 44 R 45 )— and —Y—CH 2 —CH 2 —Y′—, wherein:

Y and Y′ each represent, independently of each other, O, S or NH,

n is equal to 2 or 3,

R 42 and R 43 , each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group, and

R 44 and R 45 each represent, independently of each other, a (C 1 -C 6 )alkyl or an aryl group;

L represents a bond, or a group selected from the group consisting of:

R 2 and R 3 each represent, independently of each other, a hydrogen atom, a halogen atom, a (C 1 -C 6 ) alkyl, (C 1 -C 6 )haloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )alkyl, heteroaryl-(C 1 -C 6 )alkyl, cycloalkyl, cycloalkyl-(C 1 -C 6 )alkyl, heterocycle, heterocycle-(C 1 -C 6 )alkyl, OR 49 or NR 51 R 52 group;

L represents:

and

R f and R 2 , and R g and R 3 form together with the carbon atoms that carry them a cycloalkenyl or aryl group;

wherein:

X represents O, S or NR 57 ,

Y represents OR 58 , SR 59 or NR 60 R 61 ,

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,

R k and R 1 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group,

R m represents a (C 1 -C 20 )alkyl group,

R r represents a hydrogen atom or a (C 1 -C 6 )alkyl group,

R p and R q each represent, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, an aryl or heteroaryl group,

R 57 to R 65 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;

A − represents a monovalent, organic or inorganic anion,

with the proviso that when R 1 and R 4 are the same, and R 0 is:

wherein Z represents C,

at least one of R a and R e is not the same as R 1 .

22. The chromophore according to claim 21 , wherein the chromophore is a dye.

Assignments (3)

CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBER 16930208 PREVIOUSLY RECORDED AT REEL: 060390 FRAME: 0122. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Jan 11, 2023

From: UNIVERSITE DE PARIS

To: UNIVERSITÉ PARIS CITÉ

Reel/Frame 062387/0489 →

CHANGE OF NAME Recorded Jun 20, 2022

From: UNIVERSITE DE PARIS

To: UNIVERSITÉ PARIS CITÉ

Reel/Frame 060390/0122 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 8, 2021

From: LAINE, PHILIPPE; POULARD, LAURÉLIE; DUPEYRE, GRÉGORY; MARVAUD, VALERIE

To: SORBONNE UNIVERSITE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE PARIS

Reel/Frame 055864/0979 →

Priority Claims (1)

EP 18305891 · Jul 5, 2018 · regional

Continuity (1)

Related Publication 20210122742A1 · Apr 29, 2021