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 alkyl;

each R 4 is independently

X=N, O or S;

R 5 is methyl;

each R 6a , R 6b , R 6c is independently selected from the group comprising: 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 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 —CH 2 —CH 2 — and join 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 comprising: 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 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 comprising R or —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 or S; and

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

3. 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.

4. The compound according to claim 1 , wherein each R 3 is independently alkyl and each R 4 is independently

5. The compound according to claim 1 , wherein each R 3 is independently alkyl and each R 4 is independently

6. The compound according to claim 1 , wherein R 3 is independently

a first R 4 group is

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

7. The compound according to claim 1 , wherein each R 3 is independently

and each R 4 is independently

8. The compound according to claim 1 , wherein R 3 is independently

and each R 4 is independently

9. The compound according to claim 1 , wherein R 3 is independently

and each R 4 is independently

10. The compound according to claim 1 , wherein R 3 is independently

a first R 4 group is

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

11. The compound according to claim 1 , wherein R 3 is independently

and each R 4 is independently

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

13. The compound according to claim 1 , wherein X and Z are S.

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

15. A compound selected from the group of: