# US 2014/0197361 A1 · DICHROIC-PHOTOCHROMIC 2H-NAPHTHO[1,2-b]PYRAN COMPOUNDS AND DEVICES

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- Number: US 2014/0197361 A1
- Document ID: US20140197361A1
- Status: Published application
- Kind: A1
- Application number: 14/215,902
- Filed: 2014-03-17
- Published: 2014-07-17
- Earliest claimed: 2006-10-20
- Assignees: Alphamicron Incorporated
- Applicants: AlphaMicron Incorporated
- Inventors: Ludmila Sukhomlinova; Linli Su; Tamas Kosa; Bahman Taheri
- Web page: https://patentgrep.com/patent/US20140197361A1

## CPC

- C07D 311/92: Naphthopyrans; Hydrogenated naphthopyrans
- C09K 19/60: Pleochroic dyes
- G02B 1/041: {Lenses}
- G02B 5/23: Photochromic filters
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

A naphthopyran compound represented by the formula B1 and B2 are selected independently from the group consisting of a phenyl, naphthyl, or heterocyclic aromatic group, or may combine to form one or more aromatic rings. B1 and B2 may further include one or more substituents. R3, R4, R5, R6, and R16 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, or —NRbRc; or wherein R5 and R6 combine to form a cyclic group. Ra may include an alkyl, polycycloalkyl, alkenyl, polyalkenyl, haloalkyl, perhaloalkyl, alkynyl, polyalkynyl, hydroxyalkynyl, polyhydroxyalkynyl; or (C3-20)cycloalkyl group. Rb and Rc may include hydrogen or alkyl groups, or may combine to form a saturated heterocyclic group, or together with an adjacent phenyl group may form a julolidinyl group. R7 is a mesogenic group. And the naphthopyran, which may be referred to as a dichroic-photochromic compound, may be incorporated into an optical article.

## Claims

### Claim 1

A naphthopyran compound represented by the formula (I)
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, —Ra, —OH, —ORa, —SH, —SRa, —SORa, —SO2Ra, —NRaRa, —NRbRc, —CN, —NO2, —CO—Ra, —O—CO—Ra, and —CO2Ra, 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; 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 R3, R4, R5, R6, and R10 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc; or wherein R5 and R6 combine to form a cyclic group, and wherein R7 is a mesogenic group represented by one of the following formulas:
wherein R8 is selected from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —SH, —SRa, —NH2, —NRbRc, —CO—Ra, —O—CO—Ra, and —CO2Ra, wherein R9 is selected from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc; or wherein an R8 and R9 combine to form a cyclic 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 an ester, —Rd—, —O—, —ORd—, —ORdO—, —OCORd—, —OCORdO—, —S—, —CH═CH—, —CH═N—, —C≡C—, and —N═N—, 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.

### Claim 2 (depends on 1)

The naphthopyran compound of claim 1, wherein the compound in a UV activated state has an order parameter greater than 0.5.

### Claim 3 (depends on 1)

The naphthopyran compound of claim 1, wherein the compound in a UV activated state has an order parameter greater than 0.6.

### Claim 4 (depends on 1)

The naphthopyran compound of claim 1, wherein the compound is represented by the formula II
wherein R1, R2, and R8 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —SH, —SRa, —NH2, —NRbRc, —CO—Ra, —O—CO—Ra, and —CO2Ra, 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; 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,
n1 is an integer from 0 to 5,
n2 is an integer from 0 to 5,
p is an integer from 0 to 5,
m is an integer from 0 to 4,
each R3, R4, R5, R6, and R9 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc; or wherein any two or more of R5, R6, and R9 combine to form a cyclic group.

### Claim 5 (depends on 1)

The naphthopyran compound of claim 1, wherein the compound is represented by the formula III,
wherein R1, R2, and R8, are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —SH, —SRa, —NH2, —NRbRc, —CO—Ra, —O—CO—Ra, and —CO2Ra, 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; 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,
n1 is an integer from 0 to 5,
n2 is an integer from 0 to 5,
p is an integer from 0 to 5,
m is an integer from 0 to 4,
each R3, R4, R5, R6, and R9 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc; or wherein any two or more of R5, R6, and R9 combine to form a cyclic group, and wherein X1 is a covalent bond, and X2 and X3, identical or different from each other, are covalent bonds or linking units wherein each said linking unit is selected from the group consisting of an ester, —Rd—, —O—, —ORd—, —ORdO—, —OCORd—, —OCORdO—, —S—, —CH═CH—, —CH═N—, —C≡C—, and —N═N—, wherein Rd is a linear or branched (C1-18) alkyl or a linear or branched (C1-18)haloalkyl group.

### Claim 6 (depends on 1)

The naphthopyran compound of claim 1, represented by one of the formulas (m) to (y):

### Claim 7 (depends on 1)

The naphthopyran compound of claim 1, wherein X1, X2 or X3, identical or different from each other, is a linking unit selected from an ester having the formula —O—CO— or —COO—.

### Claim 8

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.

### Claim 9 (depends on 8)

The naphthopyran compound of claim 8, wherein the compound is represented by the formula II
wherein R1, R2, R3, R4, R5, R6, R8 and R9 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, and —NRaRa; or wherein R5 and R6 combine to form a cyclic group; or wherein R1, R2, and R8 are selected independently from the group consisting of —NRbRc;
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 n1 is an integer from 0 to 5, n2 is an integer from 0 to 5, p is an integer from 0 to 5, 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.

### Claim 10 (depends on 8)

The naphthopyran compound of claim 8, wherein the compound is represented by the formula III,
wherein R1, R2, R3, R4, R5, R6, R8, R9 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —Ra, —O—CO—Ra, —CO—Ra, —CO2Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, and —NRaRa; or wherein R1, R2, and R8 are selected independently from the group consisting of —NRbRc, or wherein R5 and R6 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 n1 is an integer from 0 to 5, n2 is an integer from 0 to 5, p is an integer from 0 to 5, m is an integer from 0 to 4;
and 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.

### Claim 11 (depends on 8)

The naphthopyran compound of claim 8, wherein the compound in a UV activated state has an order parameter greater than 0.5.

### Claim 12 (depends on 8)

The naphthopyran compound of claim 8, wherein the compound in a UV activated state has an order parameter greater than 0.6.

### Claim 13 (depends on 8)

The naphthopyran compound of claim 8, wherein the compound in a UV activated state has an order parameter greater than 0.7.

### Claim 14 (depends on 1)

An optical article comprising at least one naphthopyran compound having a formula according to claim 1.

### Claim 15 (depends on 14)

The optical article of claim 14, wherein the naphthopyran compound is represented by the formula II
wherein R1, R2, and R8 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —SH, —SRa, —NH2, —NRbRc, —CO—Ra, —O—CO—Ra, and —CO2Ra, 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; 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,
n1 is an integer from 0 to 5,
n2 is an integer from 0 to 5,
p is an integer from 0 to 5,
m is an integer from 0 to 4,
each R3, R4, R5, R6, and R9 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc; or wherein any two or more of R5, R6, and R9 combine to form a cyclic group.

### Claim 16 (depends on 14)

The optical article of claim 14, wherein the naphthopyran compound is represented by the formula III,
wherein R1, R2, and R8, are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —SH, —SRa, —NH2, —NRbRc, —CO—Ra, —O—CO—Ra, and —CO2Ra, 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; 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,
n1 is an integer from 0 to 5,
n2 is an integer from 0 to 5,
p is an integer from 0 to 5,
m is an integer from 0 to 4,
each R3, R4, R5, R6, and R9 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —SRa, —NH2, —NHRa, —NRaRa, and —NRbRc; or wherein any two or more of R5, R6, and R9 combine to form a cyclic group, and wherein X1 is a covalent bond, and X2 and X3, identical or different from each other, are covalent bonds or linking units wherein each said linking unit is selected from the group consisting of an ester, —Rd—, —O—, —ORd—, —ORdO—, —OCORd—, —OCORdO—, —S—, —CH═CH—, —CH═N—, —C≡C—, and —N═N—, wherein Rd is a linear or branched (C1-18) alkyl or a linear or branched (C1-18)haloalkyl group.

### Claim 17 (depends on 12)

The optical article of claim 12, wherein the naphthopyran compound is represented by one of the formulas (m) to (y):

### Claim 18

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.

### Claim 19 (depends on 16)

The optical article of claim 16, wherein the naphthopyran compound is represented by the formula II
wherein R1, R2, R3, R4, R5, R6, R8 and R9 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, and —NRaRa; or wherein R5 and R6 combine to form a cyclic group; or wherein R1, R2, and R8 are selected independently from the group consisting of —NRbRc;
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 n1 is an integer from 0 to 5, n2 is an integer from 0 to 5, p is an integer from 0 to 5, 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.

### Claim 20 (depends on 16)

The optical article of claim 16, wherein the naphthopyran compound is represented by the formula III,
wherein R1, R2, R3, R4, R5, R6, R8, R9 are selected independently from the group consisting of hydrogen, halogen, —Ra, —OH, —ORa, —O—CO—Ra, —CO2Ra, —CN, —NO2, —SO2Ra, —SORa, —SH, —NH2, —NHR2, and —NRaRa; or wherein R1, R2, and R8 are selected independently from the group consisting of —NRbRc, or wherein R5 and R6 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 n1 is an integer from 0 to 5, n2 is an integer from 0 to 5, p is an integer from 0 to 5, m is an integer from 0 to 4;
and 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.

### Claim 21 (depends on 18)

The optical article according to claim 18, comprising a polymeric host material, and wherein the at least one naphthopyran compound is incorporated into the polymeric host material.

### Claim 22 (depends on 21)

The optical article according to claim 21, wherein the polymeric host material comprises a polymer selected from the group consisting of polyol(allyl carbonate) monomers, polyacrylates, poly(triethyleneglycol dimethacrylate), polyperfluoroacrylates, cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), polyurethanes, polycarbonates, poly(ethylene terephtalate), polystyrene, polyfluorostyrene, poly(diethylene glycol bis(alkyl carbonate)) and mixtures thereof.

### Claim 23 (depends on 18)

The optical article according to claim 18, further comprising an optical substrate and at least one film or coating, and wherein said film or coating comprises said at least one naphthopyran compound.

### Claim 24 (depends on 23)

The optical article according to claim 23, wherein said at least one film or coating includes an anisotropic film or coating comprising an oriented polymer layer and said at least one naphthopyran compound.

### Claim 25 (depends on 23)

The optical article according to claim 23, wherein said optical substrate is selected from the group consisting of ophthalmic elements and devices, display elements and devices, windows, mirrors, and lenses.

### Claim 26 (depends on 18)

The optical article according to claim 18, wherein the article includes a mixture of a fluid, mesomorphous or gel host medium and said at least one naphthopyran compound, wherein said naphthopyran compound is dissolved or dispersed within the host medium.

### Claim 27 (depends on 26)

The optical article according to claim 26, wherein the fluid, mesomorphous, or gel host medium includes an organic solvent, a liquid crystal, a polymer, or mixtures thereof.