Nonlinear optical chiral compounds and devices incorporating same
View Patent ↗The present disclosure is in part directed to optical devices for modulating light comprising compounds which spontaneously align. The disclosure is also directed to electro-optic compounds wherein chromophore substituents are chemically bound to a chiral polymer. In one embodiment, the chiral polymer comprises a binaphthyl monomeric unit.
1. An optically active compound comprising:
a) a polymer comprising a monomeric unit comprising a binaphthyl moiety; and
b) a chromophore chemically bonded to said monomeric unit;
wherein said optically active compound has non-centrosymmetric symmetry.
2. The optically active compound of claim 1 , wherein said binaphthyl moiety is selected from the group consisting of binaphthyl, binaphthol, 1,1′-binaphthyl-2-ol-2′-amine, and 1,1′-binaphthyl-2,2′-diamine.
3. The optically active compound of claim 1 , wherein said binaphthyl moiety further comprises an alkyl moiety.
4. The optically active compound of claim 1 , wherein said binaphthyl moiety comprises an alkynyl group.
5. The optically active compound of claim 1 , wherein said monomeric unit is selected from the structures represented by formulas I and II:
wherein
Y represents independently for each occurrence a bond, alkyl, alkenyl, or alkynyl;
R 1 represents independently for each occurrence H, alkyl, or alkoxy;
R 2 represents independently for each occurrence N(R 1 ), O, S, Se or alkylene;
R 3 represents independently for each occurrence H, alkyl, or said chromophore;
R 4 represents independently for each occurrence H, alkyl or said chromophore; and
q is in the range 1 to 7 inclusive.
6. The optically active compound of claim 5 , wherein R 1 is —O-alkyl.
7. The optically active compound of claim 6 , wherein R 1 is —O-hexyl.
8. The optically active compound of claim 1 , wherein R 3 is alkyl.
9. The optically active compound of claim 6 , wherein R 3 is —O-hexyl.
10. The optically active compound of claim 8 , wherein R 2 is O.
11. The optically active compound of claim 1 , wherein R 4 an alkyl-chromophore moiety.
12. The optically active compound of claim 1 , wherein said monomeric unit is represented by the structure:
wherein
Y represents independently for each occurrence alkyl or alkynyl;
CHR represents said chromophore;
p is in the range 0 to 7 inclusive; and
q is in the range 1 to 7 inclusive.
13. The optically active compound of claim 1 , wherein said polymer comprises at least about five monomeric units.
14. The optically active compound of claim 12 , wherein said polymer comprises at least about two monomeric units.
15. The optically active compound of claim 12 , wherein q is in the range of 1 to 3.
16. The optically active compound of claim 12 , wherein q is 1.
17. The optically active compound of claim 12 , wherein greater than about 5% of said monomeric units are functionalized with a chromophore.
18. The optically active compound of claim 1 , wherein said monomeric unit comprises two chromophores.
19. The optically active compound of claim 1 , wherein said compound exhibits an electro-optic coefficient of greater than about 10 pm/V.
20. A nonlinear optical polymer selected from group consisting of formulas I and II:
wherein
Y represents independently for each occurrence a bond, alkyl, alkenyl, or alkynyl;
R 1 represents independently for each occurrence H, alkyl, or alkoxy;
R 2 represents independently for each occurrence N(R 1 ), O, S, Se or alkylene;
R 3 represents independently for each occurrence H, alkyl, or a chromophore;
R 4 represents independently for each occurrence H, alkyl or a chromophore;
n is an integer from 1 to about 100; and
q is in the range 1 to 7 inclusive.
21. The nonlinear optical polymer of claim 20 , wherein n is about 5 to about 20.
22. The nonlinear optical polymer of claim 20 , wherein R 4 is a chromophore for at least one monomeric unit of said polymer.
23. The nonlinear optical polymer of claim 21 , wherein R 1 is —O-alkyl.
24. The nonlinear optical polymer of claim 23 , wherein R 1 is —O-hexyl.
25. The nonlinear optical polymer of claim 20 , wherein R 3 is alkyl.
26. The nonlinear optical polymer of claim 25 , wherein R 3 is —O-hexyl.
27. The nonlinear optical polymer of claim 24 , wherein R 2 is O.
28. The nonlinear optical polymer of claim 25 , wherein R 4 is an alkyl-chromophore moiety.
29. The nonlinear optical polymer of claim 25 , wherein the percentage of monomeric units of said polymer functionalized with one or more chromophores is greater than about 5%.
30. The nonlinear optical polymer of claim 25 , wherein R 2 is O, and Y is an alkyl.
31. The nonlinear optical polymer of claim 25 , wherein R 2 is O, and Y is an alkynyl.
32. The nonlinear optical polymer of claim 20 , wherein said polymer is represented by the structure:
wherein
CHR represents for each occurrence a chromophore;
p is an integer in the range 0 to 7 inclusive;
x is 1 to about 50; and
n is about 10 to about 50.
33. The nonlinear optical polymer of claim 20 , wherein said polymer exhibits an electro-optic coefficient of greater than about 10 pm/V.
34. The nonlinear optical polymer of claim 20 , wherein the weight percent of chromophore is greater than about 10%.
35. A polymer composition comprising:
a) a polymer comprising at least one monomeric unit represented by formula I or II:
wherein
Y represents independently for each occurrence a bond, alkyl, alkenyl, or alkynyl;
R 1 represents independently for each occurrence H, alkyl, or alkoxy;
R 2 represents independently for each occurrence N(R 1 ), O, S, Se or alkylene;
R 3 represents independently for each occurrence H, alkyl, or a chromophore;
R 4 represents independently for each occurrence H, alkyl or a chromophore;
q is in the range 1 to 7 inclusive; and
b) a chromophore.
36. The polymer composition of claim 35 , wherein said chromophore is pendantly bound to at least one said monomeric unit.