Probing structure-property relationships in third-order nonlinear optical polymers: Third harmonic generation spectroscopy and theoretical modeling of systematically derivatized conjugated aromatic polyimines

Industrial and Engineering Chemistry Research

Volumn 38, Issue 5, 1999, Pages 1759-1774

  Yang, Chen Jen ^a   Jenekhe, Samson A ^a   Meth, Jeffrey S ^b   Vanherzeele, Herman ^b  

^a UNIVERSITY OF ROCHESTER   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMERS; FLUORESCENCE; FOUR WAVE MIXING; HARMONIC GENERATION; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; OPTICAL MATERIALS; OPTICAL PROPERTIES; PHOTONS;

POLYIMINES; RANDOM COPOLYMERS; THIRD HARMONIC GENERATION SPECTROSCOPY;

AROMATIC POLYMERS;

POLYAMINE; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; MODEL; REFRACTION INDEX; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032961842     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie970581+     Document Type: Article

References (124)

1. (a) Gibbs, H. M., Khitrova, G., Peygambarian, N., Eds. Nonlinear Photonics; Springer-Verlag: New York, 1990.
2. (b) Agrawal, G. P., Boyd, R. W., Eds. Contemporary Nonlinear Optics; Academic: Boston, 1992.
3. (c) Sauteret, C.; Hermann, J.-P.; Frey, R.; Pradere, F.; Ducuing, J.; Baughman, R. H.; Chance, R. R. Phys. Rev. Lett. 1976, 36, 956-959.
4. (a) Jenekhe, S. A., Wynne, K. J., Eds. Photonic and Optoelectronic Polymers; American Chemical Society: Washington, DC, 1997.
5. (b) Jenekhe, S. A., Ed. Macromolecular Host - Guest Complexes: Optical, Optoelectronic, and Photorefractive Properties and Applications; Material Research Society: Pittsburgh, 1992.
6. (a) Nonlinear Optical Properties of Organic Materials; Proceedings of SPIE; Vol. 3147, in press.
7. (b) Hornak, L. A., Ed. Polymers for Lightwave and Integrated Optics: Technology and Applications; Marcel Dekker: New York, 1992.
8. (c) Marder, S. R., John, J. E., Stucky, G. D., Eds. Materials for Nonlinear Optics: Chemical Perspectives; American Chemical Society: Washington, DC, 1991.
9. (d) Brédas, J. L., Silbey, R., Eds. Conjugated Polymers: The Novel Science and Technology of Highly Conductive and Nonlinear Optically Active Materials; Kluwer Academic: Dordrecht, The Netherlands, 1991.
10. (e) Prasad, P. N.; William, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; John Wiley: New York, 1991.
11. (f) Brédas, J. L., Chance, R. R., Eds. Conjugated Polymeric Materials: Opportunity in Electronics, Optoelectronics, and Molecular Electronics; Klumer Academic: Dordrecht, The Netherlands, 1990.
12. (g) Messier, J., Kajzar, F., Prasad, P., Ulrich, D., Eds. Nonlinear Optical Effects in Organic Polymers; Kluwer Academic: Dordrecht, The Netherlands, 1989.
13. Chemla, D. S., Zyss, J., Eds. Nonlinear Optical Properties of Organic Molecules and Crystals; Academic: New York, 1987; Vols. 1 and 2.
14. Brédas, J. J.; Adant, C.; Tackx, P.; Persoons, A.; Pierce, B. M. Chem. Rev. 1994, 94, 243-278.
15. Fischer, G. L.; Boyd, R. W.; Gehr, R. J.; Jenekhe, S. A.; Osaheni, J. A.; Sipe, J. E.; Weller-Brophy, L. A. Phys. Rev. Lett. 1995, 74, 1871-1874.
16. (a) Dalton, L. R. Nature 1992, 359, 269.
17. (b) Dalton, L. R.; Sapochak, L. S.; Yu, L. J. Phys. Chem. 1993, 97, 2871-2883.
18. (c) Rodenberger, D. C.; Heflin, J. R.; Garito, A. F. Nature 1992, 359, 309-311.
19. (d) Rodenberger, D. C.; Heflin, J. R.; Garito, A. F. Phys. Rev. A 1995, 51, 3234-3245.
20. (a) Marder, S. R.; Torruellas, W. E.; Blanchard-Desce, M.; Ricci, V.; Stegmen, G. I.; Gilmour, S.; Brédas, J. L.; Li, J.; Bublitz, G. U.; Boxer, S. G. Science 1997, 276, 1233-1236.
21. (b) Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, J. W.; Bourhill, G.; Brédas, J. L.; Pierce, B. M. Science 1994, 265, 632-635.
22. (c) Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J. L. J. Am. Chem. Soc. 1994, 116, 10703-10714.
23. (a) Craig, G. S. W.; Cohen, R. E.; Schrock, R. R.; Silbey, R. J.; Puccetti, G.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1993, 115, 860-867.
24. (b) Samuel, I. D. W.; Ledoux, I.; Dhenaut, C.; Zyss, J.; Fox, H. H.; Schrock, R. R.; Sibley, R. J. Science 1994, 265, 1070-1072.
25. (a) Torruellas, W. E.; Neher, D.; Zanoni, R.; Stegeman, G. I.; Kajzar, F.; Leclerc, M. J. Opt. Soc. Am. B 1995, 12, 882-888.
26. (b) Murato, H.; Takada, N.; Tsutsui, T.; Saito, S.; Kurihara, T.; Kaino, T. J. Appl. Phys. 1991, 70, 2915-2920.
27. Lawrence, B.; Torruellas, W. E.; Cha, M.; Sundheimer, M. L.; Stegeman, G. I.; Meth, J.; Etemad, S.; Baker, G. Phys. Rev. Lett. 1994, 73, 597-600.
28. (a) Fann, W.-S.; Benson, S.; Madey, J. M. J.; Etemad, S.; Baker, G. L.; Kajzar, F. Phys. Rev. Lett. 1989, 62, 1492-1495.
29. (b) Vijaya, R.; Murti, Y. V. G. S.; Rae, T. A. P.; Sundararajan, G. J. Appl. Phys. 1991, 69, 3429-3431.
30. Kanetake, T.; Ishikawa, K.; Hasegawa, T.; Koda, T.; Takeda, K.; Hasegawa, M.; Kubodera, K.; Kobayashi, H. Appl. Phy. Lett. 1989, 54, 2287-2289.
31. (a) Kaino, T.; Kobayashi, H.; Kubodera, K.-I.; Kurihara, T.; Saito, S.; Tsutsui, T.; Tokito, S. Appl. Phys. Lett. 1989, 54, 1619-1621.
32. (b) Rao, D. N.; Chopra, P.; Ghoshal, S. K.; Swiatkiewicz, J.; Prasad, P. N. J. Chem. Phys. 1986, 84, 7049.
33. (a) Swiatkiewicz, J.; Prasad, P. N.; Karasz, F. E.; Druy, M. A.; Glatkowski, P. Appl. Phy. Lett. 1990, 56, 892-894.
34. (b) Sugiyama, T.; Wada, T.; Sasabe, H. Synth. Met. 1989, 28, C323.
35. (c) Kaino, T.; Kubodera, K.; Kobayashi, H.; Kurihara, T.; Saito, S.; Tsutsui, T.; Tokito, S.; Murata, H. Appl. Phys. Lett. 1988, 53, 2002-2004.
36. Houlding, V. H.; Nahata, A.; Yardley, J. T.; Elsenbaumer, R. L. Chem. Mater. 1990, 2, 169-172.
37. (a) Kaino, T.; Kubodera, K-I.; Tomaru, S.; Kurihara, T.; Saito, S.; Tsutsui, T.; Tokito, S. Electron. Lett. 1987, 23, 1095-1097.
38. (b) Bubeck, G.; Kaltbeitzel, A.; Lenz, R. W.; Neher, D.; Stenger-Smith, J. D.; Wegner, G. Ref 3c, p 143.
39. (c) Mathy, A.; Ueberhofen, K.; Schenk, R.; Gregorius, H.; Garay, R.; Müllen, K.; Bubeck, C. Phys. Rev. B 1998, 53, 4367-4376.
40. Lee, C. Y.-C.; Swiatkiewicz, J.; Prasad, P. N.; Metha, R.; Bai, S. J. Polym. 1991, 32, 1195-1199.
41. (a) Yu, L. P.; Dalton, L. R. Synth. Met. 1989, 29, E463-E470.
42. (b) Yu, L. P.; Dalton, L. R. Macromolecules 1990, 23, 3439-3444.
43. (a) Lindle, J. R.; Bartoli, F. J.; Hoffman, C. A.; Kim, O.-K.; Lee, Y. S.; Shirk, J. S.; Kafafi, Z. H. Appl. Phys. Lett. 1990, 56, 712-714.
44. (b) Yu, L. P.; Chen, M.; Dalton, L. R. Chem. Mater. 1990, 2, 649-659.
45. (a) Osaheni, J. A.; Jenekhe, S. A.; Vanherzeele, H.; Meth, J. S. Chem. Mater. 1991, 3, 218-221.
46. (b) Agrawal, A. K.; Jenekhe, S. A.; Vanherzeele, H.; Meth, J. S. Chem. Mater. 1991, 3, 765-768.
47. (c) Jenekhe, S. A.; Yang, C. J.; Vanherzeele, H.; Meth, J. S. Chem. Mater. 1991, 3, 985-988.
48. (a) Agrawal, A. K.; Jenekhe, S. A.; Vanherzeele, H.; Meth, J. S. J. Phys. Chem. 1992, 96, 2837-2843.
49. (b) Osaheni, J. A.; Jenekhe, S. A.; Vanherzeele, H.; Meth, J. S.; Sun, Y.; MacDiarmid, A. G. J. Phys. Chem. 1992, 96, 2830-2836.
50. Jenekhe, S. A.; Osaheni, J. A.; Meth, J. S.; Vanherzeele, H. Chem. Mater. 1992, 4, 683-687.
51. Messier, J. Ref 3g, pp 47-60.
52. (a) Torruellas, W. E.; Neher, D.; Zanoni, R.; Stegeman, G. I.; Kajzar, F.; Leclerc, M. Chem. Phys. Lett. 1990, 175, 11-16.
53. (b) Torruellas, W. E.; Rochford, K. B.; Zanoni, R.; Aramaki, S.; Stegeman, G. I. Opt. Commun. 1991, 82, 94-100.
54. (c) Aramaki, S.; Torruella, W.; Zanoni, R.; Stegeman, G. I. Opt. Commun. 1991, 85, 527-535.
55. (a) Agrawal, G. P.; Cojan, C.; Flytzanis, C. Phys. Rev. B 1978, 17, 776-789.
56. (b) Rustagi, K. C.; Ducuing, J. Opt. Commun. 1974, 10, 258-261.
57. (c) Mehendale, S. C.; Rustagi, K. C. Opt. Commun. 1979, 28, 359-362.
58. Flytzanis, C. Ref 4, pp 121-135.
59. (a) Zhao, M. T.; Singh, B. P.; Prasad, P. N. J. Chem. Phys. 1988, 89, 5535-5541.
60. (b) Prasad, P. N.; Perrin, E.; Samoc, M. J. Chem. Phys. 1989, 91, 2360-2365.
61. (c) Zhao, M. T.; Samoc, M.; Singh, B. P.; Prasad, P. N. J. Phys. Chem. 1989, 93, 7916-7920.
62. Heflin, J. R.; Wong, K Y.; Zamani-Khamiri, O.; Garito, A. F. Phys. Rev. B 1988, 38, 1573-1576.
63. (a) Mukamel, S.; Wang, H. X. Phys. Rev. Lett. 1992, 69, 65-68.
64. (b) Wang, H. X.; Mukamel, S. J. Chem. Phys. 1992, 97, 8019-8036.
65. (a) Pierce, B. M. Proc. SPIE 1991, 1560, 148-161.
66. (b) Dirk, C. W.; Herndon, W. D.; Cervantes-Lee, F.; Selnau, H.; Martinex, S.; Kalamegham, P.; Tan, A.; Campos, G.; Velez, M.; Zyss, J.; Ledoux, I.; Cheng, L. T. J. Am. Chem. Soc. 1995, 117, 2214-2225.
67. (a) Reinhardt, B. A.; Unroe, M. R.; Evers, R. C.; Zhao, M.; Samoc, M.; Prasad, P. N.; Sinsky, M. Chem. Mater. 1991, 3, 864-871.
68. (b) Zhao, M.; Samoc, M.; Prasad, P. N.; Reinhardt, B. A.; Undoe, M. R.; Prazak, M.; Evers, R. C.; Kane, J. J.; Jariwala, C.; Sinsky, M. Chem. Mater. 1990, 2, 670-678.
69. Margulis, Vl. A.; Tomilin, O. B. Synth. Met. 1996, 79, 207-214.
70. (a) Osaheni, J. A.; Jenekhe, S. A. J. Am. Chem. Soc. 1995, 117, 7389-7398.
71. (b) Chen, X. L.; Jenekhe, S. A. Macromolecules 1998, 29, 6189-6192.
72. (a) Jenekhe, S. A.; Johnson, P. O.; Agrawal, A. K. Macromolecules 1989, 22, 3216-3222.
73. (b) Jenekhe, S. A.; Johnson, P. O. Macromolecules 1990, 23, 4419-4429.
74. (c) Roberts, M. F.; Jenekhe, S. A Chem. Mater. 1990, 2, 224-226.
75. (d) Roberts, M. F.; Jenekhe, S. A. Chem. Mater. 1990, 2, 629-631.
76. (e) Roberts, M. F.; Jenekhe, S. A. Macromolecules 1991, 24, 3142-3146.
77. (a) Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1991, 3, 878-887.
78. (b) Yang, C. J.; Jenekhe, S. A. Macromolecules 1995, 28, 1180-1196.
79. Vanherzeele, H.; Meth, J. S.; Jenekhe, S. A.; Roberts, M. F. J. Opt. Soc. Am. B 1992, 9, 524-533.
80. Meth, J. S.; Vanherzeele, H.; Jenekhe, S. A.; Yang, C. J.; Roberts, M. F.; Agrawal, A. K. SPIE Proc. 1991, 1560, 13-24.
81. Morgan, P. W.; Kwolek, S. L.; Pletcher, T. C. Macromolecules 1987, 20, 729-739.
82. Swanepoel, R. J. Opt. Soc. Am. A 1986, 2, 1339-1343.
83. (a) Manifacier, J. C.; Gasiot, J.; Fillard, J. P. J. Phys. E: Sci. Instrum. 1978, 9, 1002-1004.
84. (b) Manifacier, J. C.; de Murcia, M.; Fillard, J. P. Thin Solid Films 1977, 41, 127-135.
85. (a) Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1994, 6, 196-203.
86. (b) Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1995, 7, 1276-1285.
87. Vanherzeele, H. Appl. Opt. 1990, 29, 2246-2258.
88. Bethune, D. S. J. Opt. Soc. Am. B 1989, 6, 910-916.
89. Neher, D.; Wolf, A.; Bubeck, C.; Wegner, G. Chem. Phys. Lett. 1989, 163, 116-122.
90. Buchalter, B.; Meredith, G. R. Appl. Opt. 1982, 21, 3221-3224.
91. Orr, B. J.; Ward, J. F. Mol. Phys. 1971, 20, 513-526.
92. Langhoff, P. W.; Epstein, G. W.; Karplus, M. Rev. Mod. Phys. 1972, 44, 602-644.
93. Kuzyk, M. G.; Dirk, C. W. Phys. Rev. A 1990, 41, 5098-5109.
94. Dixit, S. N.; Guo, D.; Mazumdar, S. Mol. Cryst. Liq. Cryst. 1991, 194, 33-41.
95. Soos, Z. G.; McWilliams, P. C. M.; Hayden, G. W. Chem. Phys. Lett. 1990, 171, 14-18.
96. McWilliams, P. C. W.; Hayden, G. W.; Soos, Z. G. Phys. Rev. B 1991, 43, 9777-9791.
97. Wu, J. W.; Heflin, J. R.; Norwood, R. A.; Wong, K. Y.; Zamani-Khamir, O.; Garito, A. F. J. Opt. Soc. Am. B 1989, 6, 707-720.
98. (a) Guo, D.; Mazumdar, S.; Stegeman, G. I.; Cha, M.; Neher, D.; Aramaki, S.; Torruellas, W. E.; Zanoni, R. Mater. Res. Soc. Symp. Proc. 1991, 247, 151-162.
99. (b) Guo, D.; Mazumdar, S.; Dixit, S. N. Synth. Met. 1992, 49-50, 1-11.
100. (c) Kawabe, Y.; Jarka, F.; Peygambarian, N.; Guo, D.; Mazumdar, S.; Dixit, S. N.; Kajzar, F. Phys. Rev. B 1991, 44, 6530-6533.
101. Burgi, H. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1969, 472-473.
102. Odian, G.; Yang, N.-L.; Wei, Y. Magnetic Reson. Chem. 1985, 23, 908-915.
103. (a) Yang, C.-J.; Jenekhe, S. A. Ref 2b, pp 197-204.
104. (b) Yang, C.-J.; Jenekhe, S. A.; Meth J. S.; Vanherzeele, H. Polym. Adv. Technol. 1994, 5, 161-170.
105. (a) Kanabara, H.; Kobayashi, H.; Kaino, T.; Ooba, N.; Kurihara, T. J. Phys. Chem. 1994, 98, 12270-12277.
106. (b) Geisler, T.; Petersen, J. C.; Bjornholm, T.; Fischer, E.; Larsen, J.; Dehu, C.; Brédas, J. L.; Tormos, G. V.; Nugara, P. N.; Cava, M. P.; Metzger, R. M. J. Phys. Chem. 1994, 98, 10102-10111.
107. (a) Li, H. H. J. Phys. Chem. Ref. Data 1976, 5, 329-528.
108. (b) Grossman, C. H.; Garito, A. F. Mol. Cryst. Liq. Cryst. 1989, 168, 255-267.
109. Mattoussi, H.; Scrinivasarao, M.; Kaatz, P. G.; Berry, G. C. Macromolecules 1992, 25, 2860-2868.
110. Lauchlan, L.; Etemad, S.; Chung, T. C.; Heeger, A. J.; MacDiarmid, A. G. Phys. Rev. B 1981, 24, 3701-3711.
111. (a) Bradley, D. D. C.; Friend, R. H. J. Mol. Electron. 1989, 5, 19-24.
112. (b) Rauscher, U.; Bässler, H.; Bradley, D. D. C.; Hennecke, M. Phys. Rev. B 1990, 42, 9830-9836.
113. (c) Rauscher, U.; Schutz, L.; Greiner, A.; Bässler, H. J. Phys.: Condens. Matter 1989, 1, 9751-9763.
114. Jenekhe, S. A.; Osaheni, J. A. Science 1994, 265, 765-768.
115. Press: W. H.; Flannerg, B. D.; Teukolsky, S. A.; Vetterling, W. T. Numeral Recipe: The Art of Scientific Computing; Cambridge University: New York, 1988.
116. (a) Marder, S. R.; Beratan, D. N.; Cheng, L.-T. Science 1991, 252, 103-106.
117. (b) Cheng, L.-T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631-10643.
118. (c) Marder, S. R.; Perry, J. W.; Bourhill, G.; Gorman, C. B.; Tiemann, B. G.; Mansour, K. Science 1993, 261, 186-189.
119. McCoy, R. K.; Karasz, F. E. Chem. Mater. 1991, 3, 941-947.
120. Laermer, F.; Elsaesser, T.; Kaiser, W. Chem. Phys. Lett. 1988, 148 119-124.
121. (a) Tarkka, R. M.; Jenekhe, S. A. Chem. Phys. Lett. 1996, 260, 533-538.
122. (b) Tarkka, R. M.; Zhang, X.; Jenekhe, S. A. J. Am. Chem. Soc. 1996, 178, 9438-9439.
123. Loudon, R. The Quantum Theory of Light, 2nd ed.; Oxford University: New York, 1983; pp 26-30.
124. Zhou, Q. L.; Shi, R. F.; Zamani-Khamari, O.; Garito, A. F. Nonlinear Opt. 1993, 6, 145-154.