Nonlinear optical properties of dicyanomethylene-derived heteroaromatic dyes: Semiempirical molecular orbital calculations and experimental investigations

International Journal of Quantum Chemistry

Volumn 79, Issue 4, 2000, Pages 253-266

  Zerner, Michael C ^a   Fabian, Walter M F ^b   Dworczak, Renate ^b   Kieslinger, Dietmar W ^c   Kroner, Gert ^b   Junek, Hans ^b   Lippitsch, Max E ^c  

^a UNIVERSITY OF FLORIDA   (United States)

^b UNIVERSITY OF GRAZ   (Austria)

^c UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

APPROXIMATION THEORY; AROMATIC COMPOUNDS; COMPOSITION EFFECTS; COMPUTATIONAL METHODS; CONFORMATIONS; HYDROGEN BONDS; ISOMERS; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; NONLINEAR OPTICS; OPTICAL PROPERTIES; SOLVENTS;

DICYANOMETHYLENE; HETEROAROMATIC DYES; HYPERPOLARIZABILITY; ISOMERISM; MOLECULAR ORBITAL (MO) METHOD;

DYES;

EID: 0034275245     PISSN: 00207608     EISSN: None     Source Type: Journal    
DOI: 10.1002/1097-461X(2000)79:4<253::AID-QUA6>3.0.CO;2-K     Document Type: Article

References (123)

1. (a) Junek, H.; Klade, M.; Sterk, H.; Fabian, W. Monatsh Chem 1988, 119, 993.
2. (b) Junek, H.; Klade, M. Dyes Pigments 1988, 9, 393.
3. (c) Junek, H.; Dworczak, R.; Sterk, H.; Fabian, W. Liebigs Ann Chem 1989, 1065.
4. (d) Dworczak, R.; Fabian, W. M. R; Sterk, H.; Kratky, C.; Junek, H. Liebigs Ann Chem 1992, 7.
5. (e) Dworczak, R.; Glaser, H.; Biza, P.; Junek, H. Dyes Pigments 1993, 21, 75.
6. (f) Reidlinger, C.; Dworczak, R.; Fabian, W. M. F.; Junek, H. Dyes Pigments 1994, 24, 185.
7. (g) Dworczak, R.; Fabian, W. M. F.; Biza, P.; Weikmann, M.; Junek, H. Dyes Pigments 1995, 28, 297.
8. (h) Fabian, W. M. F.; Dworczak, R.; Junek, H.; Pawar, B. N. J Chem Soc Perkin Trans 2 1995, 903.
9. (i) Dworczak, R.; Fabian, W. M. F.; Pawar, B. N.; Junek, H. Dyes Pigments 1995, 29, 65.
10. (j) Dworczak, R.; Fabian, W. M. F.; Kieslinger, D.; Junek, H. Dyes Pigments 1997, 34, 13.
11. (k) Dworczak, R.; Fabian, W. M. F.; Kieslinger, D.; Gann, G.; Junek, H. Dyes Pigments 1998, 36, 45.
12. (a) Marder, S. R.; Perry, J. W. Adv Mater 1993, 5, 804.
13. (b) Nie, W. Adv Mater 1993, 5, 520.
14. (c) Nalwa, H. S. Adv Mater 1993, 5, 341.
15. (d) Williams, D. J. Angew Chem 1984, 96, 637.
16. (a) Rao, V. P.; Jen, A. K. Y.; Wong, K. Y.; Drost, K. J. J Chem Soc Chem Commun 1993, 1118.
17. (b) Rao, V. P.; Cai, Y. M.; Jen, A. K. Y. J Chem Soc Chem Commun 1994, 1689.
18. (c) Jen, A. K. Y.; Rao, V. P.; Drost, K. J.; Wong, K. Y.; Cava, M. P. J Chem Soc Chem Commun 1994, 2057.
19. (a) Wong, K. Y.; Jen, A. K. Y.; Rao, V. P.; Drost, K. J. J Chem Phys 1994, 100, 6818.
20. (b) Ortiz, R.; Marder, S. R.; Cheng, L.-T.; Tiemann, B. G.; Cavagnero, S.; Ziller, J. W. J Chem Soc Chem Commun 1994, 2263.
21. (c) Wong, M. S.; Meier, U.; Pan, F.; Gramlich, V.; Bosshard, C.; Günther, P. Adv Mater 1996, 8, 416.
22. (d) Dulcic, A.; Flytzanis, C.; Tang, C. L.; Pepin, D.; Fetizon, M.; Hoppilliard, Y. J Chem Phys 1981, 74, 1559.
23. (a) Blanchard-Desce, M.; Lehn, J. M.; Barzoukas, M.; Ledoux, I.; Zyss, J. Chem Phys 1994, 181, 281.
24. (b) Puccetti, G.; Blanchard-Desce, M.; Ledoux, I.; Lehn, J. M.; Zyss, J. J Phys Chem 1993, 97, 9385.
25. (c) Ulman, A. J Phys Chem 1988, 92, 2385.
26. (a) Calabrese, J. C.; Cheng, L.-T.; Green, J. C.; Marder, S. R.; Tam, W. J Am Chem Soc 1991, 113, 7227.
27. (b) Marder, S. R.; Beratan, D. N.; Cheng, L.-T. Science 1991, 252, 103.
28. (c) Marder, S. R.; Gorman, C. B.; Tiemann, B. G.; Cheng, L.-T. J Am Chem Soc 1993, 115, 3006.
29. (d) Risser, S. M.; Beratan, D. N.; Marder, S. R. J Am Chem Soc 1993, 115, 7719.
30. (e) Bourhil, G.; Bredas, J. L.; Cheng, L.-T.; Marder, S. R.; Meyers, F.; Perry, J. W.; Tieman, B. G. J Am Chem Soc 1994, 116, 2619.
31. (f) Sen, R.; Majumdar, D.; Bhattacharyya, S. P.; Bhattacharyya, S. N. J Phys Chem 1993, 97, 7491.
32. (a) Cheng, L.-T.; Tam, W.; Stevenson, S. H.: Meredith, G. R.; Rikken, G.; Marder, S. R. J Phys Chem 1991, 95, 10631.
33. (b) Cheng, T-L.; Tarn, W.; Marder, S. R.; Stiegman, A. E.; Rikken, G.; Spangler, C. W. J Phys Chem 1991, 95, 10643.
34. (c) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem Rev 1994, 94, 195.
35. (a) Docherty, V. J.; Pugh, D.; Morley, J. O. J Chem Soc Faraday Trans 2 1985, 81, 1179.
36. (b) Morley, J. O.; Docherty, V. J.; Pugh, D. J Chem Soc Perkin Trans 2 1987, 1351, 1357, 1361.
37. (c) Morley, J. O.; Docherty, V. J.; Pugh, D. J Mol Electron 1989, 5, 117.
38. (d) Morley, J. O.; Pavlides, P.; Pugh, D. J Chem Soc Faraday Trans 2 1989, 85, 1789.
39. (e) Hurst, M.; Munn, R. W.; Morley, J. O. J Mol Electron 1990, 6, 15.
40. (f) Morley, J. O. J Am Chem Soc 1988, 110, 7660.
41. (g) Morley, J. O.; Pavlides, P.; Pugh, D. Int J Quantum Chem 1992, 43, 7.
42. (h) Morley, J. O. J Chem Soc Perkin Trans 2 1989, 103.
43. (i) Morley, J. O. Int J Quantum Chem 1993, 46, 19.
44. (j) Morley, J. O. J Chem Soc Faraday Trans 1991, 87, 3009, 3015.
45. (k) Morley, J. O.; Pugh, D. J Chem Soc Faraday Trans 1991, 87, 3021.
46. (l) Morley, J. O. J Chem Soc Perkin Trans 2 1994, 1211.
47. (m) Morley, J. O. J Chem Soc Faraday Trans 1994, 90, 1849, 1853.
48. (n) Albert, I. D. L.; Morley, J. O.; Pugh, D. J Chem Phys 1993, 99, 5197.
49. (a) Kanis, D. R.; Marks, T. J.; Ratner, M. A. Int J Quantum Chem 1992, 43, 61.
50. (b) Kanis, D. R.; Ratner, M. A.; Marks, T. J. J Am Chem Soc 1992, 114, 10338.
51. (c) Li, D. Q.; Ratner, M. A.; Marks, T. J. J Am Chem Soc 1988, 110, 1707.
52. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J.; Zerner, M. C. Chem Mater 1991, 3, 19.
53. (e) Di Bella, S.; Fragala, I. L.; Ratner, M. A.; Marks, T. J. J Am Chem Soc 1993, 115, 682.
54. (f) Li, D. Q.; Marks, T. J.; Ratner, M. A. J Phys Chem 1992, 96, 4325.
55. (g) Kanis, D. R.; Ratner, M. A.; Marks, T. J. J Am Chem Soc 1990, 112, 8203.
56. (h) Di Bella, S.; Ratner, M. A.; Marks, T. J. J Am Chem Soc 1992, 114, 5842.
57. (i) Di Bella, S.; Marks, T. J.; Ratner, M. A. J Am Chem Soc 1994, 116, 4440.
58. (j) Dehu, C.; Meyers, F.; Hendrickx, E.; Clays, K.; Persoons, A.; Marder, R. S.; Bredas, J. L. J Am Chem Soc 1995, 117, 10127.
59. (a) Jain, M.; Chandrasekhar, J. J Phys Chem 1993, 97, 4044.
60. (b) Yoshimura, T. Phys Rev B 1989, 40, 6292.
61. (c) Yoshimura, T. Appl Phys Lett 1989, 55, 534.
62. (d) Yoshimura, T. Mol Cryst Liq Cryst 1990, 182A, 43.
63. (e) Pierce, B. M. J Chem Phys 1989, 91, 791.
64. (a) Andraud, C.; Brotin, T.; Garcia, C.; Pellé, F.; Goldner, P.; Bigot, B.; Collet, A. J Am Chem Soc 1994, 116, 2094.
65. (b) Dehu, C.; Meyers, F.; Bredas, J. L. J Am Chem Soc 1993, 115, 6198.
66. (c) Dirk, C. W.; Twieg, R. J.; Wagniere, G. J Am Chem Soc 1986, 108, 5387.
67. (d) Ulman, A.; Willand, C. S.; Köhler, W.; Robello, D. R.; Williams, D. J.; Handley, L. J Am Chem Soc 1990, 112, 7083.
68. Itoh, Y.; Ohno, K.; Isogai, M.; Kakuta, A. Mol Cryst Liq Cryst 1989, 170, 259.
69. (b) Ohno, K.; Itoh, Y.; Hamada, T.; Isogai, M.; Kakuta, A. Mol Cryst Liq Cryst 1990, 182A, 17.
70. (a) Zyss, J. J Chem Phys 1979, 70, 3333, 3341.
71. (b) Zyss, J. J Chem Phys 1979, 71, 909.
72. (a) Dewar, M. J. S.; Yamaguchi, Y. Chem Phys Lett 1978, 59, 541.
73. (b) Williams, G. R. J. J Mol Struct 1987, 151 (Theochem 36), 215.
74. (c) Williams, G. R. J. J Mol Struct 1987, 153 (Theochem 38), 185, 191.
75. (a) Kurtz, H. A.; Stewart, J. J. P.; Dieter, K. M. J Comput Chem 1990, 11, 82.
76. (b) Barzoukas, M.; Fort, A.; Boy, P.; Combellas, C.; Thiebault, A. Chem Phys 1994, 185, 65.
77. (c) Matsuzawa, N.; Dixon, D. A. J Phys Chem 1992, 96, 6232, 6241.
78. (d) Matsuzawa, N.; Dixon, D. A. J Phys Chem 1994, 98, 2545.
79. (e) Hammoutene, D.; Boucekkine, G.; Boucekkine, A.; Berthier, G. J Mol Struct 1993, 287 (Theochem 106), 93.
80. (f) Chandra, A. K.; Banerjee, M. J Mol Struct 1991, 251 (Theochem 83), 261.
81. (a) Meyers, F.; Adant, C.; Bredas, J. L. J Am Chem Soc 1991, 113, 3715.
82. (b) Meyers, F.; Bredas, J. L.; Zyss, J. J Am Chem Soc 1992, 114, 2914.
83. (c) Bredas, J. L.; Meyers, F.; Pierce, B. M.; Zyss, J. J Am Chem Soc 1992, 114, 4928.
84. (d) Meyers, F.; Bredas, J. L. Int J Quantum Chem 1992, 42, 1595.
85. (a) Bader, M. M.; Hamada, T.; Kakuta, A. J Am Chem Soc 1992, 114, 6475.
86. (b) Hinchliffe, A.; Soscun, H. J. J Mol Struct 1994, 304 (Theochem 110), 109.
87. (a) Waite, J.; Papadopoulos, M. G.; Nicolaides, C. A. J Chem Phys 1982, 77, 2527, 2536.
88. (b) Waite, J.; Papadopoulos, M. G. J Comput Chem 1983, 4, 578.
89. (c) Waite, J.; Papadopoulos, M. G. J Chem Phys 1984, 80, 3503.
90. (d) Papadopoulos, M. G.; Waite, J. J Phys Chem 1986, 90, 5491.
91. (e) Papadopoulos, M. G.; Waite, J. J Chem Soc Faraday Trans 1990, 86, 3525.
92. (f) Waite, J.; Papadopoulos, M. G. J Phys Chem 1990, 94, 1755, 6244.
93. (a) Karna, S. P.; Dupuis, M. Chem Phys Lett 1990, 171, 201.
94. (b) Karna, S. P.; Dupuis, M. J Comput Chem 1991, 12, 487.
95. (c) Keshari, V.; Karna, S. P.; Prasad, P. N. J Phys Chem 1993, 97, 3525.
96. (a) Baker, J. D.; Zerner, M. C. J Phys Chem 1991, 95, 8614.
97. (b) Parkinson, W. A.; Oddershede, J. J Chem Phys 1991, 94, 7251.
98. (c) Champagne, B.; Mosley, D. H.; Andre, J. M. Int J Quantum Chem 1993, S27, 667.
99. (d) Champagne, B.; Mosley, D. H.; Fripiat, J. G.; Andre, J. M. Int J Quantum Chem 1993, 46, 1.
100. (e) Williams, G. R. J. J Mol Struct 1993, 283 (Theochem 102), 185.
101. (f) Weiss, H.; Ahlrichs, R.; Haser, M. J Chem Phys 1993, 99, 1262.
102. (g) Guidotti, C.; Lamanna, U. T.; Arrighini, G. P.; Durante, N. J Mol Struct 1992, 254 (Theochem 86), 77.
103. (h) Luo, Y.; Agren, H.; Vahtras, O.; Jorgensen, P. Chem Phys Lett 1993, 207, 190.
104. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J Am Chem Soc 1985, 107, 3902.
105. (b) Stewart, J. J. P. MOPAC 6.0, QCPE program no. 455.
106. (c) Clark, T. VAMP 4.4; Erlangen Vectorized Molecular Orbital Package; Computer-Chemie-Centrum, University Erlangen-Nürnberg, Germany, 1992.
107. (a) Ridley, J.; Zerner, M. C. Theor Chim Acta 1973, 32, 111.
108. (b) Zerner, M. C. ZINDO, A Comprehensive Semiempirical Quantum Chemistry Package; Quantum Theory Project, Gainesville, Florida, 1993.
109. (d) Tapia, O.; Goscinski, O. Mol Phys 1975, 29, 1653.
110. (a) Karelson, M. M.; Zerner, M. C. J Phys Chem 1992, 96, 6949.
111. (b) Szafran, M.; Karelson, M. M.; Katritzky, A. R.; Koput, J.; Zerner, M. C. J Comput Chem 1993, 14, 371.
112. (c) Yu, J.; Zerner, M. C. J Chem Phys 1994, 100, 7487.
113. (a) Singer, K. D.; Garito, A. F. J Chem Phys 1981, 75, 3572.
114. (b) Levine, B. F.; Bethea, C. G. J Chem Phys 1975, 63, 2666.
115. (c) Uemiya, T.; Uenishi, N.; Umegaki, S. J Appl Phys 1993, 99, 12.
116. (d) Hermann, W. N.; Hayden, L. M. J Opt Soc Am B 1995, 12, 416.
117. For caveats in comparing calculated and experimental hyperpolarizabilities see Willetts, A.; Rice, J. R.; Burland, D. M.; Shelton, D. P. J Chem Phys 1992, 97, 7590.
118. (a) Stewart, J. J. P. J Comput Chem 1989, 10, 221.
119. (b) Dewar, M. J. S.; Healy, E. F.; Holder, A. J.; Yuan, Y-C. J Comput Chem 1990, 11, 541.
120. Parkinson, W. A.; Zerner, M. C. J Chem Phys 1991, 94, 478.
121. Fabian, W. M. F. J Comput Chem 1988, 9, 369.
122. Stähelin, M.; Burland, D. M.; Rice, J. E. Chem Phys Lett 1992, 191, 245.
123. Kieslinger, D. W. Master thesis, Institut für Experimental-physik, Karl-Franzens Universität Graz, 1995.