DICHROIC-PHOTOCHROMIC 2H-NAPHTHO[1,2-b]PYRAN COMPOUNDS AND DEVICES

A naphthopyran compound represented by the formula (I)

• wherein R7 is a mesogenic group represented by one of the following formulas:
• wherein R3, R4, R5, R6, R8, R9 and R10 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CO—Ra, —CO2Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc;
• or wherein R5 and R6 combine to form a cyclic group;
• or wherein R8 and R9 combine to form a cyclic group;
• wherein Ra is a linear or branched (C1-20) alkyl, (C3-20) cycloalkyl, (C4-20) polycycloalkyl linear or branched (C1-20) alkenyl, linear or branched (C1-20) polyalkenyl, linear or branched (C1-20) haloalkyl, perhaloalkyl group, linear or branched (C1-20) alkynyl, linear or branched (C1-20) polyalkynyl, linear or branched (C1-20) hydroxyalkynyl, linear or branched (C1-20) polyhydroxyalkynyl;
• and Rb and Rc are independently selected from the group consisting of hydrogen and linear or branched (C1-20) alkyl groups, or wherein Rb and Rc combine to form a saturated 5- to 7-member heterocyclic group, or wherein Rb and Rc together and in combination with an adjacent phenyl group form a julolidinyl group;
• wherein p is an integer from 0 to 5, wherein m is an integer from 0 to 4;
• wherein X1, X2 and X3, identical or different from each other, represent a covalent bond or linking unit selected from the group consisting of —O—CO—, —COO—, —Rd—, —O—, —ORd—, —ORdO—, —OCORd—, —OCORdO—, —S—, —CH═CH—, —CH═N—, —C≡C—, —N═N—, NHRa, and NRaRa, wherein Rd is a linear or branched (C1-18) alkyl or a linear or branched (C1-18)haloalkyl group, and wherein Y is oxygen, nitrogen, or sulfur;
• wherein B1 and B2 are selected independently from the group consisting of (i) a phenyl group, (ii) a naphthyl group, (iii) a heterocyclic aromatic group, and (iv) a combination thereof, or wherein B1 and B2 optionally combine to form one or more aromatic rings;
• wherein B1 and B2 are optionally substituted with one or more substituents selected from the group consisting of halogen, —Re, —OH, —ORe, —SH, —SRe, —SORe, —SO2Re, —NReRe, —NRbRc, —CN, —NO2, —CO—Re, —O—CO—Re, and —CO2Re, wherein Re is a linear or branched (C1-20) alkyl, (C3-20) cycloalkyl, (C4-20) polycycloalkyl linear or branched (C1-20) alkenyl, linear or branched (C1-20) polyalkenyl, linear or branched (C1-20) haloalkyl, perhaloalkyl group, linear or branched (C1-20) alkynyl, linear or branched (C1-20) polyalkynyl, linear or branched (C1-20) hydroxyalkynyl, linear or branched (C1-20) polyhydroxyalkynyl, a phenyl group, a naphthyl group, a heterocyclic aromatic group, or a combination thereof.

An optical article comprising at least one naphthopyran compound is represented by the formula (I)

• wherein R7 is a mesogenic group represented by one of the following formulas:
• wherein R3, R4, R5, R6, R8, R9 and R10 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CO2Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc;
• or wherein R5 and R6 combine to form a cyclic group;
• or wherein R8 and R9 combine to form a cyclic group;
• wherein Ra is a linear or branched (C1-20) alkyl, (C3-20) cycloalkyl, (C4-20) polycycloalkyl linear or branched (C1-20) alkenyl, linear or branched (C1-20) polyalkenyl, linear or branched (C1-20) haloalkyl, perhaloalkyl group, linear or branched (C1-20) alkynyl, linear or branched (C1-20) polyalkynyl, linear or branched (C1-20) hydroxyalkynyl, linear or branched (C1-20) polyhydroxyalkynyl;
• and Rb and Rc are independently selected from the group consisting of hydrogen and linear or branched (C1-20) alkyl groups, or wherein Rb and Rc combine to form a saturated 5- to 7-member heterocyclic group, or wherein Rb and Rc together and in combination with an adjacent phenyl group form a julolidinyl group;
• wherein p is an integer from 0 to 5, wherein m is an integer from 0 to 4;
• wherein X1, X2 and X3, identical or different from each other, represent a covalent bond or linking unit selected from the group consisting of —O—CO—, —COO—, —Rd—, —O—, —ORd—, —ORdO—, —OCORd—, —OCORdO—, —S—, —CH═CH—, —CH═N—, —C≡C—, —N═N—, NHRa, and NRaRa, wherein Rd is a linear or branched (C1-18) alkyl or a linear or branched (C1-18)haloalkyl group, and wherein Y is oxygen, nitrogen, or sulfur;
• wherein B1 and B2 are selected independently from the group consisting of (i) a phenyl group, (ii) a naphthyl group, (iii) a heterocyclic aromatic group, and (iv) a combination thereof, or wherein B1 and B2 optionally combine to form one or more aromatic rings;
• wherein B1 and B2 are optionally substituted with one or more substituents selected from the group consisting of halogen, —Re, —OH, —ORe, —SH, —SRe, —SORB, —SO2Re, —NReRe, —NRbRc, —CN, —NO2, —CO—Re, —O—CO—Re, and —CO2Re, wherein Re is a linear or branched (C1-20) alkyl, (C3-20) cycloalkyl, (C4-20) polycycloalkyl linear or branched (C1-20) alkenyl, linear or branched (C1-20) polyalkenyl, linear or branched (C1-20) haloalkyl, perhaloalkyl group, linear or branched (C1-20) alkynyl, linear or branched (C1-20) polyalkynyl, linear or branched (C1-20) hydroxyalkynyl, linear or branched (C1-20) polyhydroxyalkynyl, a phenyl group, a naphthyl group, a heterocyclic aromatic group, or a combination thereof.