Synthesis and characterization of thiazole-containing chromophores for second-order nonlinear optics

Journal of Materials Chemistry

Volumn 9, Issue 7, 1999, Pages 1449-1452

  Wang, Yuh Kai ^a   Shu, Ching Fong ^a   Breitung, Eric M ^b   McMahon, Robert J ^b  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; OPTICS; REACTION ANALYSIS; SYNTHESIS;

EID: 0032794081     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900820i     Document Type: Article

References (31)

1. 1 (a) P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, John Wiley & Sons, New York, 1991;
2. (b) Molecular Nonlinear Optics: Materials, Physics and Devices, ed. J. Zyss, Academic Press, Boston, 1993;
3. (c) D. R. Kanis, M. A. Ratner and T. J. Marks, Chem. Rev., 1994, 94, 195;
4. (d) Polymers for Second Order Nonlinear Optics, eds. G. A. Lindsay and K. D. Singer, ACS Symposium Series Vol. 601, American Chemical Society, Washington, DC, 1995.
5. 2 (a) L. T. Cheng, W. Tam, S. R. Marder, A. E. Steigman, G. Rikken and C. W. Spangler, J. Phys. Chem., 1991, 95, 10643;
6. (b) L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen and K. J. Shea, Chem. Mater., 1995, 7, 1060;
7. (c) M. S. Wong, Ch. Bosshard, F. Pan and P. Günter, Adv. Mater., 1996, 8, 677;
8. (d) M. Blanchard-Desce, V. Alain, P. V. Bedworth, S. R. Marder, A. Fort, C. Runser, M. Barzoukas, S. Lebus and R. Wortmann, Chem. Eur. J., 1997, 3, 1091.
9. 3 (a) V. P. Rao, A. K.-Y. Jen, K. Y. Wong and K. J. Drost, Tetrahedron Lett., 1993, 34, 1747;
10. (b) A. K.-Y. Jen. V. P. Rao, K. Y. Wong and K. J. Drost, J. Chem. Soc., Chem. Commun., 1993, 90;
11. (c) V. P. Rao, A. K.-Y. Jen, K. Y. Wong and K. J. Drost, J. Chem. Soc., Chem. Commun., 1993, 1118;
12. (d) S.-S. P. Chou, D.-J. Sun, H.-C. Lin and P.-K. Yang, Tetrahedron Lett., 1996, 37, 7279;
13. (e) C.-F. Shu, W.-J. Tsai, J.-Y. Chen, A. K.-Y. Jen, Y. Zhang and T.-A. Chen, J. Chem. Soc., Chem. Commun., 1996, 2279.
14. 4 (a) C. W. Dirk, H. E. Katz, M. L. Schilling and L. A. King, Chem. Mater., 1990, 2, 700;
15. (b) R. D. Miller, V. Y. Lee and C. R. Moylan, Chem. Mater., 1994, 6, 1023.
16. 5 (a) P. R. Varanasi, A. K.-Y. Jen, J. Chandrasekhar, I. N. N. Namboothiri and A. Rathna, J. Am. Chem. Soc., 1996, 118, 12443;
17. (b) I. D. L. Albert, T. J. Marks and M. A. Ratner, J. Am. Chem. Soc., 1997, 119, 6575.
18. 6 C.-F. Shu and Y.-K. Wang, J. Mater. Chem., 1998, 8, 833.
19. 7 T. L. Gilchrist, Heterocyclic Chemistry, John Wiley & Sons Inc., New York, 1985.
20. 8 A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici and P. Pedrini, Tetrahedron, 1988, 44, 2021.
21. 9 (a) C. M. Whitaker, E. V. Patterson, K. L. Kott and R. J. McMahon, J. Am. Chem. Soc., 1996, 118, 9966;
22. (b) K. L. Kott, C. M. Whitaker and R. J. McMahon, Chem. Mater., 1995, 7, 426.
23. 10 MOPAC version 6.0, Quantum Chemistry Program Exchange, (QCPE #455), Department of Chemistry, Indiana University, Bloomington, Indiana.
24. 11 A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici and P. Pedrini, Synthesis, 1987, 998.
25. 12 A. I. de Lucas, N. Martín, P. de Miguel, C. Seoane, A. Albert and F. H. Cano, J. Mater. Chem., 1995, 5, 1145.
26. 13 (a) C. R. Moylan, R. L. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton and R. D. Miller, J. Am. Chem. Soc., 1993, 115, 12599;
27. (b) P. V. Bedworth, Y. Cai, A. Jen and S. R. Marder, J. Org. Chem., 1995, 61, 2242;
28. (c) C.-F. Shu, Y.-C. Shu, Z.-H. Gong, S.-M. Peng, G. H. Lee and A. K.-Y. Jen, Chem. Mater., 1998, 10, 3284.
29. 14 A. K.-Y. Jen, Y. Cai, P. V. Bedworth and S. R. Marder, Adv. Mater., 1997, 9, 132.
30. 3a,b
31. -1 above the lowest energy conformer, this conformer was used for the purpose of remaining consistent with the other compounds. It should be noted that the computed dipole moment of 5 differs from that of the lowest energy conformer by only 0.2 D.