Naphthopyrans annelated in C6-C7, their preparation and compositions and (CO)polymer matrices containing them

Naphthopyrans of the following formula (I):

• in which:
• L corresponds to a direct bond or to a divalent residue selected from the group consisting of O;
• S;
• NR6, where R6 represents a linear or branched alkyl group which comprises 1 to 6 carbon atoms;
• CR7R8;
• (CR7R8)2;
• R7C=CR8, where R7 and R8 are identical or different and independently represent a H, an OH group, or a linear or branched alkyl or alkoxy group which comprises 1 to 6 carbon atoms;
• and a carbocycle selected from the following:
• R1 and R2 independently represent:
• a hydrogen,
• a linear or branched alkyl group which comprises 1 to 12 carbon atoms,
• a cycloalkyl group which comprises 3 to 12 carbon atoms,
• an aryl group which comprises in its basic structure 6 to 24 carbon atoms or a heteroaryl group which comprises in its basic structure 4 to 24 carbon atoms and at least one heteroatom selected from sulphur, oxygen and nitrogen;
• said basic structure being optionally substituted with at least one substituent selected from:
• a halogen,
• a hydroxy group,
• a linear or branched alkyl group comprising 1 to 12 carbon atoms,
• a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
• a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
• a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
• an —NH2 group,
• an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
• a
• group, where R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or represent together with the nitrogen atom to which they are bound a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group, which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
• a methacryloyl group or an acryloyl group,
• an aralkyl or heteroaralkyl group, the alkyl group, which is linear or branched, comprising 1 to 4 carbon atoms and the aryl and heteroaryl groups having the definitions given above, or
• said two substituents R1 and R2 together form an adamantyl, norbornyl, fluorenylidene, di(C1-C6)alkylanthracenylidene or spiro(C5-C6)cyclo-alkylanthracenylidene group;
• said group being optionally substituted with at least one of the substituents listed above for R1, R2:
• an aryl or heteroaryl group;
• R3 and R4, which are identical or different, independently represent:
• a hydrogen,
• a halogen,
• a linear or branched alkyl group which comprises 1 to 12 carbon atoms,
• a cycloalkyl group comprising 3 to 12 carbon atoms,
• a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
• a haloalkyl, halocycloalkyl, or haloalkoxy group corresponding to the alkyl, cycloalkyl, alkoxy groups above respectively, which are substituted with at least one halogen atom,
• an aryl or heteroaryl group having the same definition as that given above for R1, R2,
• an aralkyl or heteroaralkyl group, the alkyl group, which is linear or branched, comprising 1 to 4 carbon atoms, and the aryl and heteroaryl groups having the same definitions as those given above for R1, R2,
• an amine or amide group:
• —NH2, —NHR, —CONH2, —CONHR,
• R, R′, R″ having their respective definitions given above for the amine substituents of R1, R2:
• aryl or heteroaryl,
• an —OCOR6 or —COOR6 group, R6 representing a straight or branched alkyl group comprising 1 to 6 carbon atoms, or a cycloalkyl group comprising 3 to 6 carbon atoms, or a phenyl group, optionally substituted with at least one of the substituents listed above for the values of R1, R2:
• aryl or heteroaryl;
• m and n are, independently, integers of 0 to 4 and of 0 to 3 respectively;
• R5 represents:
• a hydrogen,
• a linear or branched alkyl group which comprises 1 to 12 carbon atoms,
• a cycloalkyl group which comprises 3 to 12 carbon atoms,
• a linear or branched alkenyl group which comprises 2 to 12 carbon atoms,
• a phenyl or benzyl group, optionally substituted with at least one of the substituents listed above for R1, R2:
• aryl or heteroaryl,
• a —COR7, —COOR7, or CONHR7 group, R7 representing a linear or branched alkyl group comprising 1 to 6 carbon atoms, or a cycloalkyl group comprising 3 to 6 carbon atoms, or a phenyl or benzyl group optionally substituted with at least one of the substituents listed above in the definition of the radicals R1, R2 in formula (I), in the case in which these radicals correspond independently to an aryl or heteroaryl group.