Asymmetrization effects on structures and populations of the ground state of dipolar donor-acceptor-substituted molecular organic NLO materials

Journal of Computational Chemistry

Volumn 19, Issue 10, 1998, Pages 1130-1140

  Glaser, Rainer ^a   Chen, Grace Shiahuy ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

Asymmetrization effects; Dipole alignment; Electron donor acceptor; Materials for nonlinear optics; Population analysis; Structural effects of conjugation

Indexed keywords

EID: 0001212076     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(19980730)19:10<1130::AID-JCC2>3.0.CO;2-N     Document Type: Article

References (34)

1. J. Zyss, Ed., Molecular Nonlinear Optics, Materials, Physics, and Devices, Academic Press, New York, 1994.
2. H. Kuhn and J. Robillard, Eds., Nonlinear Optical Materials, CRC Press, Boca Raton, FL, 1992.
3. G. P. Agrawal and R. W. Boyd, Eds., Contemporary Nonlinear Optics, Academic Press, New York, 1992.
4. P. S. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, John Wiley & Sons, New York, 1991.
5. S. R. sarder, J. E. Sohn, and G. D. Stucky, Eds., Materials for Nonlinear Optics, Chemical Perspectives (ACS Symposium Series 455), American Chemical Society, Washington, DC, 1991.
6. C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, and P. Günter, Organic Nonlinear Optical Materials, Advances in Nonlinear Optics, Vol. 1, Gordon and Breach, New York, 1995.
7. (a) M. L. H. Green, S. R. Marder, M. E. Thompson, J. A. Bandy, D. Bloor, P. V. Kolinsky, and R. J. Jones, Nature, 330, 360 (1987);
8. (b) W. Tam and J. C. Calabrese, Chem. Phys. Lett., 144, 79 (1988).
9. T. Marks and M. A. Ratner, Angew. Chem. Int. Ed. Engl., 34, 155 (1995).
10. (a) S. Tamaru, S. Zambutsu, M. Kawachi and M. Kobayashi, J. Chem. Soc., Chem. Commun., 1207 (1984);
11. (b) D. F. Eaton, A. G. Anderson, W. Tam, and Y. Wang, J. Am. Chem. Soc., 109, 1886 (1987);
12. (c) W. Tam, S. F. Eaton, J. C. Calabrese, I. D. Williams, Y. Wang, and A. G. Anderson, Chem. Mater., 1, 128 (1989);
13. (d) R. Hoss, O. Koenig, V. Kramer-Hoss, U. Berger, P. Borgin, and J. Hulliger, Angew. Chem. Int. Ed. Engl., 35, 1664 (1996).
14. R. Glaser, D. Steiger, and C. Ahlbrandt, manuscript in preparation.
15. G. R. Desiraju, Angew. Chem. Int. Ed. Engl., 34, 2311 (1995).
16. (a) J. H. Williams, Acc. Chem. Res., 26, 593 (1993);
17. (b) P. Hobza, H. L. Selzle, and E. W. Schlag, Chem. Rev., 94, 1767 (1994).
18. For the use of polyazines as third-order NLO materials, see: H. S. Nalwa, T. Hamada, A. Kakuta, and A. Mukoh, Synthet. Metals, 55-57, 3901 (1993).
19. G. S. Chen, Ph.D. Dissertation, University of Missouri-Columbia, 1996.
20. R. E. Glaser and G. S. Chen, Dipole Aligned Molecular Materials, U.S. patent application filed.
21. Complete dipole alignment also was recently realized in a ferromagnetic material, see: A. J. Banister, N. Bricklebank, I. Lavender, J. M. Rawson, W. Clegg, M. R. K. Elsegood, and F. Palacio, Angew. Chem. Int. Ed. Engl., 35, 2533 (1996). According to ab initio calculations (R. Glaser and D. Farmer, to be published), the fluorinated 1,2,3,5-dithiazolyl radical has a dipole moment of about 4.6 Debye.
22. Complete dipole alignment also was recently realized in a ferromagnetic material, see: A. J. Banister, N. Bricklebank, I. Lavender, J. M. Rawson, W. Clegg, M. R. K. Elsegood, and F. Palacio, Angew. Chem. Int. Ed. Engl., 35, 2533 (1996). According to ab initio calculations (R. Glaser and D. Farmer, to be published), the fluorinated 1,2,3,5-dithiazolyl radical has a dipole moment of about 4.6 Debye.
23. R. Glaser, G. S. Chen, and C. L. Barnes, J. Org. Chem., 58, 7446 (1993).
24. G. S. Chen, M. Anthamatten, C. L. Barnes, and R. Glaser, J. Org. Chem., 59, 4336 (1994).
25. G. S. Chen, M. Anthamatten, C. L. Barnes, and R. Glaser, Angew. Chem. Int. Ed. Engl., 33, 1081 (1994).
26. R. Glaser, G. S. Chen, M. Anthamatten, and C. L. Barnes, J. Chem. Soc. Perkin Trans., 2 1449 (1995).
27. G. S. Chen, J. K. Wilbur, C. L. Barnes, and R. Glaser, J. Chem. Soc. Perkin Trans., 2, 2311 (1995).
28. R. Glaser and G. S. Chen, Polym. Mater. Sci. Eng., 75, 229 (1996).
29. R. Glaser, M. Lewis, and C. L. Barnes, manuscript submitted.
30. W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
31. M. J. Frisch, G W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Ciolowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, GAUSSIAN94, Revision C.3, Gaussian, Inc., Pittsbburgh, Pa, 1995.
32. E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold: NBO 3.0, Theoretical Chemistry Institute and Department of Chemistry, University of Wisconsin, Madison, WI 53706.
33. (a) S. Huzinaga, J. Andzelm, M. Klobuskowski, E. Radzio-Andzelm, Y. Sakai, and H. Tatewaki, Gaussian Basis Sets for Molecular Calculations, Elsevier, New York, 1984, p. 217, see also p. 12.
34. C. Dehu, F. Meyers, and J. L. Bredas, J. Am. Chem. Soc. 115, 6198 (1993).