Organic materials with special optical effects
The present invention relates to a compound of the following formula (I). The invention also relates to uses thereof as a chromophore as such or for building pigments displaying special optical effects, including metal-like reflection.
1. A metallic effect purely organic pigment material, comprising a self-assembly of a compound of following general formula (I):
wherein:
R 0 represents a hydrogen atom;
R 1 ═R 4 ═R 1 ′═R 4 ′, and R 1 represents a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, phenyl, cycloalkyl comprising from 3 to 7 carbon atoms, (CH 2 ) m OR 24 , or OR 26 , wherein m is equal to 1, 2 or 3;
or
R 4 and R 4 ′ form together a bond or a chain selected from the group consisting of —C(R 74 R 75 )—, —(CH 2 ) n —, wherein:
n is equal to 2 or 3,
R 74 , R 75 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl;
R 2 ═R 2 ′, R 3 ═R 3 ′, and R 2 and R 3 each represents, a hydrogen atom;
L X =L X′ , and L X represents a bond, or a group selected from the group consisting of:
X═X′, and X represents NR 50 R 51 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, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 56 , SR 57 and NR 58 R 59 , and
said aryl is para-substituted by a group selected from NR 60 R 61 , and optionally substituted by one or more groups selected from a halogen atom, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 66 , SR 67 and NR 68 R 69 ;
or
L X =L X′ and L X represents a bond; X═X′ and X represents NR 50 ′R 51 ′; and
R 2 and NR 50 ′, and R 2 ′ and NR 50 ′ 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, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 81 , SR 82 and NR 83 R 84 ;
and
R 3 and NR 51 ′, and R 3 ′ and NR 51 ′ 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, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, OR 81 , SR 82 and NR 83 R 84 ;
and R 50 ′, R 51 ′, R 52 ′ and R 53 ′ represent respectively R 50 , R 51 , R 52 and R 53 when they are not linked with R 2 or R 3 ;
and
R 24 , R 26 , R 50 , R 51 , R 56 to R 59 , R 66 to R 69 and R 81 to R 84 each represents, independently of each other, a hydrogen atom, a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl or aryl, 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 85 , SR 86 and NR 87 R 88 group, wherein R 85 to R 88 each represent, independently of each other, a hydrogen atom or a (C 1 -C 6 )alkyl group;
and
A − represents a monovalent or multivalent, organic or inorganic anion.
2. The metallic effect purely organic pigment material according to claim 1 , wherein said compound is selected from the group consisting of:
3. The metallic effect purely organic pigment material according to claim 1 , wherein said compound is a compound of formula (I) wherein:
L X =L X′ , and L X represents a bond.
4. The metallic effect purely organic pigment material according to claim 1 , wherein A − represents a hexafluorophosphate, tetrafluoroborate, tetraphenylborate, DDQH − , halide or triflate anion.
5. The metallic effect purely organic pigment material according to claim 1 , wherein said metallic effect purely organic pigment material is a pigment.
6. The metallic effect purely organic pigment material according to claim 1 , wherein said metallic effect purely organic pigment material is a metal-like reflective coating.
7. The metallic effect purely organic pigment material according to claim 1 , wherein R 1 represents a (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, phenyl, CH 2 OR 24 , or OR 26 .