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Sterically stabilized second-order nonlinear optical chromophores with improved stability and devices incorporating the same

Imported: 24 Feb '17 | Published: 09 Sep '03

Cheng Zhang, Harold R. Fetterman, William Steier, Joseph Michael

USPTO - Utility Patents

Abstract

Sterically stabilized second-order nonlinear optical chromophores and devices incorporating the same are embodied in a variety of chromophore materials. An exemplary preferred chromophore includes an electron donor group, an electron acceptor group and a ring-locked bridge structure therebetween, with the bridge structure being directly connected to the electron donor via a single bond. Another exemplary preferred chromophore includes an electron donor group, an electron acceptor group and a ring-locked bridge structure between the electron donor group and the electron acceptor group, with two free double bonds, one located between the donor and the bridge and the other located between the (fused) ring bridge and the acceptor. Another exemplary preferred chromophore includes an electron donor group, an electron acceptor group, and a bridge structure therebetween, with the chromophores having no carbon-carbon double bond between the donor and the (fused) ring bridge. In this class, there is only one unlocked carbon-carbon double bond between the (fused) ring bridge and the acceptor. Another exemplary preferred chromophore includes an electron donor group, an electron acceptor group, and a ring-locked bridge structure therebetween, with a built-in electron-withdrawing cyano group on the last ring of the (fused) bridge. Another exemplary preferred chromophore includes any electron donor group, an electron acceptor group including a linear conjugated triene bearing four cyano groups, and any bridge structure therebetween.

Description

DESCRIPTION OF THE DRAWINGS

Other objects, features and advantages of the invention will become readily apparent upon reference to the following detailed description when considered in conjunction with the accompanying drawings, in which like reference numerals designate like parts throughout the figures thereof, and wherein:

FIG. 1 illustrates the basic structure of class I chromophores according to the present invention;

FIG. 2 illustrates the basic structure of class II chromophores according to the present invention;

FIG. 3 illustrates the basic structure of class III chromophores according to the present invention;

FIG. 4 illustrates the basic structure of class IV chromophores according to the present invention;

FIG. 5 illustrates the basic structure of new electron acceptors

4CF and

4CI;

FIG. 6 illustrates some representative electron donors used according to the present invention for synthesizing all the chromophores;

FIG. 7 illustrates ring-locked tricyano electron acceptors used for construction of some of the chromophores in the present invention;

FIG. 8 illustrates some representative electron acceptors used for construction of some of the chromophores in the present invention;

FIG. 9 illustrates an exemplary synthetic scheme of the single-ring bridged chromophore shown in FIG. 1;

FIG. 10 illustrates an exemplary synthetic scheme of the fused triple-ring bridged chromophore shown in FIG. 1;

FIG. 11 illustrates some exemplary preferred chromophores having the basic structures depicted in FIG. 1;

FIG. 12 illustrates some exemplary preferred chromophores having the basic structures depicted in FIG. 2;

FIG. 13 illustrates an exemplary synthesis of the chromophore of structure (IIb) shown in FIG. 2;

FIG. 14 illustrates some exemplary preferred chromophores having the basic structures depicted in FIG. 3;

FIG. 15 illustrates an exemplary synthesis of the chromophores shown in FIG. 3;

FIG. 16 illustrates an exemplary preferred synthetic scheme of chromophores shown in FIG. 4;

FIG. 17 illustrates an exemplary preferred electrooptic device employing a constant electric field bias, the device incorporating a chromophore material the present invention;

FIG. 18 illustrates an exemplary preferred Mach Zehnder modulator incorporating a chromophore material of the present invention;

FIG. 19 illustrates the use of a chromophore material of the present invention (in the form of microstrip lines) in a microwave phase shifter of the type employed in optically controlled phased array radars;

FIG. 20 illustrates a five-membered ring which, according to the present invention, can replace one or more of the six-membered rings in the bridges of the chromophores shown in FIGS. 1-5;

FIG. 21 illustrates a seven-membered ring which, according to the present invention, can replace one or more of the six-membered rings in the bridges of the chromophores shown in FIGS. 1-5; and

FIG. 22 illustrates a container within which an electrooptic device is hermetically packaged according to the present invention.

Claims

1. A nonlinear optical device comprising:

2. The nonlinear optical device of claim 1 wherein the electron acceptor group is formed as:

3. The nonlinear optical device of claim 1 wherein the electron acceptor group is formed as:

4. A nonlinear optical device comprising:

5. The nonlinear optical device of claim 4 wherein the bridge structure includes one or more five-membered rings.

6. The nonlinear optical device of claim 4 wherein-the bridge structure includes one or more six-membered rings.

7. The nonlinear optical device of claim 4 wherein the bridge structure includes one or more seven-membered rings.

8. A nonlinear optical device comprising:

9. A nonlinear optical device comprising:

10. A nonlinear optical device comprising:

11. The nonlinear optical device of claim 8,

9, or

10 wherein one or more of the six-membered rings in the chromophore is/are replaced by one or more five-membered or seven-membered aliphatic rings.

12. A nonlinear optical device comprising:

13. The nonlinear optical device of claim 12 wherein the ring-locked tricyano electron acceptor is formed as:

14. A nonlinear optical device comprising:

15. A nonlinear optical device comprising:

16. The nonlinear optical device of claim 15 wherein the electron donor group is formed as:

17. A nonlinear optical device comprising:

18. The nonlinear optical device of claim 17 wherein the electron withdrawing group is a cyano group.

19. The nonlinear optical device of claim 17 wherein the bridge structure includes a five-membered ring.

20. The nonlinear optical device of claim 17 wherein the bridge structure includes a six-membered ring.

21. The nonlinear optical device of claim 17 wherein the bridge structure includes a seven-membered ring.

22. A nonlinear optical device comprising:

23. A nonlinear optical device comprising:

24. The nonlinear optical device of any of claims

1-

10 and

12-

23 wherein the device is hermetically packaged in a container either vacuumed or vacuumed and then filled with an inert gas including one or more of: nitrogen, helium, neon, argon, krypton and xenon.

25. The nonlinear optical device of claim 24 wherein the container is a metal case.

26. An optical device comprising: