Naphthopyrans with a heterocycle in the 5, 6-position, preparation, and (co)polymer compositions and matrices containing them

A compound having the formula (I) or (II) below:

• in which:
• X is an oxygen or NR6, R6 being a hydrogen, a linear or branched alkyl group comprising from 1 to 12 carbon atoms, a cycloalkyl group comprising from 3 to 12 carbon atoms, an aryl group comprising in its basic structure 6 to 24 carbon atoms, or a heteroaryl group comprising in its basic structure 4 to 24 carbon atoms and at least one heteroatom selected from the group consisting of sulfur, oxygen, and nitrogen, said aryl or heteroaryl group's basic structure optionally being substituted by at least one substituent selected from the group consisting of a linear or branched alkyl comprising 1 to 12 carbon atoms, a linear or branched alkoxy comprising 1 to 12 carbon atoms, a halogen, and a hydroxy;
• R4 and R5, which are identical or different, independently represent a hydrogen, a hydroxy, or a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R4 and R5 together form an oxo group (═O);
• R1 and R2, which are identical or different, independently are:
• hydrogen,
• a linear or branched alkyl group comprising from 1 to 12 carbon atoms,
• a cycloalkyl group comprising from 3 to 12 carbon atoms,
• an aryl group comprising in its basic structure 6 to 24 carbon atoms or a heteroaryl group comprising in its basic structure 4 to 24 carbon atoms and at least one heteroatom selected from the group consisting of sulfur, oxygen, and nitrogen, said aryl or heteroaryl group's basic structure optionally being substituted with at least one substituent selected from the group consisting of:
• a halogen,
• a hydroxy,
• a linear or branched alkyl group comprising from 1 to 12 carbon atoms,
• a linear or branched alkoxy group comprising from 1 to 12 carbon atoms,
• a haloalkyl or haloalkoxy group corresponding respectively to the above (C1-C12)alkyl or (C1-C12)alkoxy groups substituted with at least one halogen atom,
• a phenoxy or naphthoxy group optionally substituted with at least one linear or branched alkyl or alkoxy group comprising from 1 to 12 carbon atoms,
• a linear or branched alkenyl group comprising from 2 to 12 carbon atoms,
• an —NH2 group,
• an —NHR group, wherein R is a linear or branched alkyl group comprising from 1 to 6 carbon atoms or a phenyl group optionally substituted by at least one linear or branched alkyl comprising from 1 to 6 carbon atoms,
• a group having the formula:
• wherein R′ and R″, identical or different, independently represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms or a phenyl group optionally substituted with at least one linear or branched alkyl comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bonded, represent a 5- to 7-membered ring which optionally comprises at least one other heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen, said nitrogen optionally being substituted with a group R′″, which is a linear or branched alkyl group comprising from 1 to 6 carbon atoms, and
• a methacryloyl group or an acryloyl group, or
• an aralkyl or heteroaralkyl group in which the alkyl part is linear or branched and comprises from 1 to 4 carbon atoms and in which the aryl or heteroaryl part is as defined above for the aryl or heteroaryl group, or
• said two substituents R1 and R2 together form an adamantyl, norbornyl, fluorenylidene, di(C1-C6)alkylanthracenylidene, or spiro(C5-C6)cycloalkylanthracenylidene group, said group being optionally substituted with at least one of the substituents listed above for R1 and R2 as an aryl or heteroaryl group;
• R3, which are identical or different, independently are:
• a halogen,
• a hydroxy,
• a linear or branched alkyl group comprising from 1 to 12 carbon atoms,
• a cycloalkyl group comprising from 3 to 12 carbon atoms,
• a linear or branched alkoxy group comprising from 1 to 12 carbon atoms,
• a haloalkyl, halocycloalkyl, or haloalkoxy group corresponding respectively to the above alkyl, cycloalkyl, and alkoxy groups substituted with at least one halogen atom,
• an aryl or heteroaryl group as defined above for R1 and R2,
• an aralkyl or heteroaralkyl group in which the alkyl part is linear or branched and comprises from 1 to 4 carbon atoms and in which the aryl or heteroaryl part is as defined above for R1 and R2,
• a phenoxy or naphthoxy group optionally substituted with at least one linear or branched alkyl or alkoxy group comprising from 1 to 12 carbon atoms,
• one of the following amine or amide groups:
• —NH2, —NHR, —CONH2, —CONHR,
• R, R′, and R″ respectively being as defined above for the amino substituents of R1 and R2 as aryl or heteroaryl, or
• a group —OCOR7 or —COOR7, wherein R7 is a linear or branched alkyl group comprising from 1 to 6 carbon atoms, a cycloalkyl group comprising from 3 to 6 carbon atoms, or a phenyl group optionally substituted with at least one of the substituents listed above for R1 and R2 as aryl or heteroaryl, or
• at least two adjacent groups R3 together form an aromatic or non-aromatic cyclic group having one ring or two fused rings which ring(s) are 5- to 7-membered, which ring(s) optionally comprise at least one heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen, and which ring(s) are optionally substituted with at least one substituent selected from those given above in the definition for the aryl or heteroaryl groups which can form R1 or R2;
• and
• m is an integer from 0 to 4.