Diarylethene compounds and uses thereof

1. A compound according to Formula IA/IB, reversibly convertible under photochromic and electrochromic conditions between a ring-open isomer A and a ring-closed isomer B:

wherein:

Z is N, O or S;

each R 1 is independently selected from H or halo;

each R 2 is independently selected from the group consisting of H, halo, a polymer backbone, alkyl, and aryl; or both R 2 together form —CH═CH—;

each R 3 is independently

 or

 wherein at least one

R 3 is

each R 4 is independently

 or

X=N, O, or S;

each R 6a , R 6b , R 6c is independently selected from the group consisting of: H, Cl, Br, F, —CF 3 , —CN, —NO 2 , methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, saturated or unsaturated alkyl that is linear or branched with 5-12carbons, —Si(R 11 ) 3 , thiophene, substituted thiophene, benzyl, substituted benzyl, —CH═CH 2 , —OCH 3 , —COH, —OH, —CO 2 H, —COCH 3 , —C(CH 3 ) 2 OH, —Si(CH 3 ) 3 , —CH 2 CH 2 OCH 3 , —CH 2 CH 2 OH, —N(CH 3 ) 2 , —CO 2 CH 3 , —OCH 2 OCH 3 , —SO 2 CH 3 , —OCH 2 C(CH 3 ) 3 , —OCH 2 CH(CH 3 ) 2 , —OC(CH 3 ) 3 , —OCH═CH 2 , —O(CH 2 ) 4 OH, —O(CH 2 ) 3 OH, —C(CH 3 ) 2 OH, —O(CH 2 ) 2 OCH 3 , —O(CH 2 ) 4 CN, —O(CH 2 ) 4 COOH,

or R 6a and R 6b are each —CH═CH— and join to form an unsaturated ring, or —CH2—CH2— and fused to form a ring;

each R 7a , R 7b , R 7c , each R 8a , R 8b , R 8c , R 8d , R 8e , and each R 9a , R 9b , R 9c , R 9d , R 9e , is independently selected from the group consisting of: H, Cl, Br, F, —CF 3 , —CN, —NO 2 , methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, saturated or unsaturated alkyl that is linear or branched with 5-12 carbons, —Si(R 11 ) 3 , thiophene, substituted thiophene, benzyl, substituted benzyl, —CH═CH—, —CH═CH 2 , —OCH 3 , —COH, —OH, —CO 2 H, —COCH 3 , —C(CH 3 ) 2 OH, —Si(CH 3 ) 3 , —CH 2 CH 2 OCH 3 , —CH 2 CH 2 OH, —N(CH 3 ) 2 , —CO 2 CH 3 , —OCH 2 OCH 3 , —SO 2 CH 3 , —OCH 2 C(CH 3 ) 3 , —OCH 2 CH(CH 3 ) 2 , —OC(CH 3 ) 3 , —OCH═CH 2 , —O(CH 2 ) 4 OH, —O(CH 2 ) 3 OH, —C(CH 3 ) 2 OH, —O(CH 2 ) 2 OCH 3 , —O(CH 2 ) 4 CN, —O(CH 2 ) 4 COOH,

n and m are independently any integer from 0 to 20;

R 11 is independently selected from the group consisting of R and —O—R, wherein:

R is a linear or branched, non-aromatic monocyclic or polycyclic, substituted or unsubstituted alkyl group comprising a carbon backbone comprising any one of 1 to 20 carbons; or

R is a heteroalkyl group comprising one or more of O, S, N, or Si; or

R is a linear or branched, saturated or unsaturated, alkyl group comprising a carbon backbone comprising any one of 1 to 12 carbons; or

R is a substituted or unsubstituted methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, pentyl or hexyl group;

at least one of R 6a , R 6b , R 6c is not H;

at least one of R 7a , R 7b , R 7c is not H;

at least one of R 8a , R 8b , R 8c , R 8d , R 8e is not H; and

at least one of R 9a , R 9b , R 9c , R 9d , R 9e is not H.

2. The compound according to claim 1 wherein:

each R 6a , R 6b , R 6c , R 7a , R 7b , and R 7c , is independently selected from a group consisting of —H, —Cl, —CN, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, —Si(R 11 ) 3 , thiophene, substituted thiophene, —CO 2 H, —COCH 3 , and —Si(CH 3 ) 3 ;

R 11 is R, wherein R is a heteroalkyl group comprising one or more of O, S; and

at least one of R 6a , R 6b , R 6c is not H.

3. The compound according to claim 1 wherein:

each R 3 is independently

 each R 4 is independently

 and

R 8c and R 9c are not all —OCH 3 or all —C(CH 3 ) 3 .

4. The compound according to claim 1 wherein R is a linear or branched alkyl group or a heteroalkyl group comprising one or more of O, S, N or Si, the alkyl group or the heteroalkyl group comprising any one of 1 to 20 carbons.

5. The compound according to claim 1 wherein:

a first R 3 group is

 and a second R 3 group is

a first R 4 group residing on the same ring moiety as the first R 3 group is

a second R 4 group residing on the same ring moiety as the second R 3 group is

 and

R 6a is not H.

6. The compound according to claim 1 wherein:

each R 3 is independently

 and each R 4 is independently

7. The compound according to claim 1 wherein R 1 and R 2 are F.

8. The compound according to claim 1 , selected from a group consisting of:

9. A compound according to Formula XA/XB, reversibly convertible under photochromic and electrochromic conditions between a ring-open isomer A and a ring-closed isomer B:

wherein:

Z is N, O or S;

each R 1 is independently H or halo;

each R 2 is independently selected from the group consisting of H, halo, a polymer backbone, alkyl and aryl; or both R 2 together form —CH═CH—;

R 3 is

 or

each R 4 is independently aryl,

 or

X═N, O, or S;

R 5 is H or alkyl;

each R 6a , R 6b , R 6c , each R 7a , R 7b , R 7c , each R 8a , R 8b , R c , R 8d , R 8e , each R 9a , R 9b , R 9c , R 9d , R 9e , is independently selected from the group consisting of: H, Cl, Br, F, —CF 3 , —CN, —NO 2 , methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, saturated or unsaturated alkyl that is linear or branched with 5 to 12carbons, —Si(R 11 ) 3 , thiophene, substituted thiophene, benzyl, substituted benzyl, —CH═CH 2 , —OCH 3 , —COH, —OH, —CO 2 H, —COCH 3 , —C(CH 3 ) 2 OH, —Si(CH 3 ) 3 , —CH 2 CH 2 OCH 3 , —CH 2 CH 2 OH, —N(CH 3 ) 2 , —CO 2 CH 3 , —OCH 2 OCH 3 , —SO 2 CH 3 , —OCH 2 C(CH 3 ) 3 , —OCH 2 CH(CH 3 ) 2 , —OC(CH 3 ) 3 , —OCH═CH 2 , —O(CH 2 ) 4 CN, —O(CH 2 ) 4 OH, —O(CH 2 ) 3 OH, —C(CH 3 ) 2 OH, —O(CH 2 ) 2 OCH 3 ,

n and m are independently any integer from 0 to 20;

R 11 is independently selected from the group consisting of R and —O—R, wherein:

R is linear or branched, non-aromatic monocyclic or polycyclic, substituted or unsubstituted alkyl group comprising a carbon backbone comprising any one of 1 to 20 carbons; or

R is a heteroalkyl group comprising one or more of O, S, N or Si; or

R is a linear or branched, saturated or unsaturated, alkyl group comprising a carbon backbone comprising any one of 1 to 12 carbons; or

R is a substituted or unsubstituted methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, pentyl or hexyl group; and

each of R 10a , R 10b , R 10c , and R 10d , is individually selected from a group consisting of an electron donating group, an electron withdrawing group, —OCH 3 , —CN, —OH, H,

 and

 or R 10b and R 10c are each O and joined by —CH 2 — to form a 5-membered ring.

10. The compound according to claim 9 wherein:

each R 6a , R 6b , R 6c , R 7a , R 7b , and R 7c , is independently selected from a group consisting of H, Cl, —CN, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl, tert-butyl, —Si(R 11 ) 3 , thiophene, substituted thiophene, —CO 2 H, —COCH 3 , —Si(CH 3 ) 3 ; and

R 11 is R, wherein R is a heteroalkyl group comprising one or more of O or S.

11. The compound according to claim 9 wherein R 3 is

a first R 4 group residing on the same ring moiety as R 3 is

and a second R 4 group residing on a different ring moiety as R 3 is

12. The compound according to claim 9 wherein R 3 is

and each R 4 is independently

13. The compound according to claim 9 wherein R 3 is

a first R 4 group residing on the same ring moiety as the R 3 is

and a second R 4 group residing on a different ring moiety as R 3 is

14. The compound according to claim 9 wherein R 3 is

and each R 4 is independently

15. The compound according to claim 9 wherein R 3 is

and each R 4 is independently

16. The compound according to claim 9 wherein R 3 is

a first R 4 group residing on the same ring moiety as R 3 is

and a second R 4 group residing on a different ring moiety as R 3 is

17. The compound according to claim 9 wherein R 3 is

a first R 4 group residing on the same ring moiety as R 3 is

and a second R 4 group residing on a different ring moiety as R 3 is

18. The compound according to claim 9 wherein R 3 is

and each R 4 is independently

19. The compound according to claim 9 wherein R 1 and R 2 are F.

20. The compound according to claim 9 , selected from a group consisting of: