Novel substituted-polyaryl chromophoric compounds

• US 20070197699A1
• Filed: 02/28/2007
• Published: 08/23/2007
• Est. Priority Date: 10/19/2000
• Status: Abandoned Application

• Current Assignee: Trans Photonics LLC
• Original Assignee: Trans Photonics LLC
• Inventors: Saadeh, Haythem, Gharavi, Alireza
• Application Number:
  US11/712,136
• Publication Number:
  US 20070197699A1
• Time in Patent Office: Days
• US Class Current: 524/190
• CPC Class Codes: C09B 29/0003 from diazotized anilines
• CPC Class Codes: C09B 29/0809 substituted amino group
• CPC Class Codes: C09B 29/12 of the benzene series
• CPC Class Codes: C09B 31/043 Amino-benzenes
• CPC Class Codes: C09B 31/062 Phenols
• CPC Class Codes: C09B 43/28 by etherification of hydroxyl groups
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02F 1/3611 containing Nitrogen
• CPC Class Codes: G02F 1/3612 Heterocycles having N as heteroatom
• CPC Class Codes: G02F 1/3613 containing Sulfur
• CPC Class Codes: G02F 1/3614 Heterocycles having S as heteroatom

Abstract

The invention provides for novel substituted-polyaryl chromophoric compounds which desirably comprise a single diazo group, and optimally include a plurality of diazo groups. Preferably the chromophores exhibit optical nonlinear second-order properties and have unique absorption maximum and other chromophoric properties that make them useful for, among other things, multifunctional optical switches or waveguides.

Claims

1-8. -8. (canceled)

9. A compound of the formula:

wherein Ar¹ is selected from the group consisting of;

Ar² is selected from the group consisting of;

and if m=1;

R¹ is an electron donating group selected from the group consisting of hydrogen, hydroxy, amino, and C_1-12alkoxy (optionally substituted with hydroxyl or amino), C_1-12dialkylamino (substituted with hydroxyl or amino), C_1-12alkylarylamino (optionally substituted with hydroxyl or amino), and diarylamino (optionally substituted with hydroxyl or amino);

R² is hydrogen, C_1-12alkyl, carboxy, hydroxy, C_1-12alkoxy, or halo; and

at least one of the groups R³, R⁴ and R⁵ is an electron withdrawing group selected from the group consisting of hydrogen, cyano, COR², C_1-12mono- or polyhaloalkyl, C_1-12alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C_1-12alkylsulfonyl (optionally substituted) and arylsulfonyl (optionally substituted);

while the other of the groups R³, R⁴ and R⁵ are, independently, C_1-12alkyl, hydroxy, C_1-12alkoxy, amino, C_1-12alkylarylamino (optionally substituted with hydroxyl or amino), diarylamino (optionally substituted with hydroxyl or amino), hydrogen, cyano, COR2, C_1-12mono- or polyhaloalkyl, C_1-12alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C_1-12alkylsulfonyl (optionally substituted), or arylsulfonyl (optionally substituted); and

if m=2-9;

R¹ is an electron donating group selected from the group consisting of hydrogen, hydroxy, amino, C_1-12alkoxy (optionally substituted with hydroxyl or amino), C_1-12dialkylamino (optionally substituted with hydroxyl or amino), C_1-12alkylarylamino (optionally substituted with hydroxyl or amino), and diarylamino (optionally substituted with hydroxyl or amino);

R² is hydrogen, C_1-12alkyl, carboxy, hydroxy, C_1-12alkoxy, or halo; and

at least one of the groups R³, R⁴ and R⁵ is an electron withdrawing group selected from the group consisting of hydrogen, cyano, COR², C_1-12mono- or polyhaloalkyl, C_1-12alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C_1-12alkylsulfonyl (optionally substituted), and arylsulfonyl (optionally substituted);

while the other of the groups R³, R⁴ and R⁵ are, independently, C_1-12alkyl, hydroxy, C_1-12alkoxy, amino, C_1-12alkylarylamino (optionally substituted with hydroxyl or amino), diarylamino (optionally substituted with hydroxyl or amino), hydrogen, cyano, COR², C_1-12mono- or polyhaloalkyl, C_1-12alkenyl (substituted with an additional electron withdrawing group), halo, nitro, sulfonyl, C_1-12alkylsulfonyl (optionally substituted), or arylsulfonyl (optionally substituted).

10. The compound in accordance with claim 9 wherein R² is hydrogen, methyl, or methoxy;

R³, R⁴ and R⁵ are, independently, hydrogen, methylsulfonyl, or nitro; and

m=2-9.

11. The compound in accordance with claim 10 wherein R³, R⁴ and R⁵ are, independently, hydrogen or nitro;

and m=2-9.

12. The compound in accordance with claim 9 wherein R³, R⁴ and R⁵ are, independently, hydrogen or methylsulfonyl;

and m=2-9.

13. A composition comprising an effective amount of the compound in accordance with claim 9 in admixture with a optically acceptable polymer.

14. A composition comprising an effective amount of the compound in accordance with claim 9 attached to a optically acceptable polymer with a C0-30 spacer.

15. A use of a compound in accordance with claim 9 in an optical waveguide or an optical switch.

16. A use of a compound in accordance with claim 9 in an optical waveguide or an optical switch.