Large Molecular Hyperpolarizabilities in "Push-Pull" Porphyrins. Molecular Planarity and Auxiliary Donor-Acceptor Effects

Chemistry of Materials

Volumn 10, Issue 3, 1998, Pages 753-762

  Albert, Israel D L ^a   Marks, Tobin J ^a   Ratner, Mark A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000257033     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm970478a     Document Type: Article

References (77)

1. (a) Polymers for Second-Order Nonlinear Optics; Lindsay, G. A.; Singer, K. D., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC 1995; Vol. 601.
2. (b) Burland, D. M.; Miller, R. D.; Walsh, C. A. Chem. Rev. 1994, 94, 31.
3. Kanis, D. R.; Ratner M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
4. Boyd, G. T.; Kuzyk, M. G. In Polymers for Electronic and Photonic Applications; Wong, C. P., Ed.; Academic Press: New York, 1993.
5. (e) Molecular Nonlinear Optics: Materials, Physics and Devices; Zyss, J., Ed.; Academic Press: Boston, 1993.
6. (a) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991.
7. (b) Brèdas, J.-L., Silbey, R. J., Eds. Conjugated Polymers: The Novel Science and Technology of Highly Conducting and Nonlinear Optically Active Materials; Kluwer: Dordrecht, 1991.
8. (a) Yitzchaik, S.; Marks, T. J. Acc. Chem. Res. 1996, 29, 197.
9. (b) Marks, T. J.; Ratner, M. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
10. Eaton, D. F.; Meridith, G. R.; Miller, J. S. Adv. Mater. 1992, 4, 45.
11. Williams, D. J. Angew. Chem., Int. Ed. Engl. 1984, 23, 690.
12. (a) Clays, K.; Persoons, A. Adv. Chem. Phys. 1994, 85, 455, Phys. Rev. Lett. 1991, 66, 2980.
13. (4) (a) Clays, K.; Persoons, A. Adv. Chem. Phys. 1994, 85, 455, Phys. Rev. Lett. 1991, 66, 2980.
14. (b) Levine, B. F.; Bethea, C. G. Appl. Phys. Lett. 1974, 24, 445.
15. Garito, A. F.; Shi, R. F.; Wu, M. H. Phys. Today 1994, 47, 51.
16. (a) Cheng, L.-T.; Tam, W.; Stevenson, S. H.; Meridith, G. R.; Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631.
17. (b). Cheng, L.-T.; Tam, W.; Marder, S. R.; Steigman, A. E.; Rikken, G.; Spangler, C. W. Ibid. 10643.
18. Albert, I. D. L.; Das, P. K.; Ramasesha, S. Chem. Phys. Lett. 1990, 168, 454.
19. Yoshimura, T. Phys. Rev. B 1989, 40, 6292.
20. (a). Albert, I. D. L.; Morley, J. O.; Pugh, D. J. Chem. Soc., Faraday Trans 2 1994, 90, 2617.
21. (b) Jain, M.; Chandrasekhar, J. J. Phys. Chem. 1993, 97, 4044.
22. (e) Matsuzawa, N.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6232.
23. Li, D.; Marks, T. J.; Ratner, M. A. J. Phys. Chem. 1992, 96, 4325.
24. (e) Morley, J. O.; Docherty, V. J.; Pugh, D. J. Chem. Soc., Perkin Trans 2 1987, 1351.
25. (f) Li, D.; Marks, T. J.; Ratner, M. A. Chem. Phys. Lett. 1986, 131, 370.
26. (g) Docherty, V. J.; Pugh, D.; Morley, J. O. J. Chem. Soc., Faraday Trans 2 1985, 81, 1179.
27. (a) Oudar, J. L. J. Chem. Phys. 1977, 67, 446.
28. (b) Oudar, J. L.; Chemla, D. S. J. Chem. Phys. 1977, 66, 2664.
29. Miller, R. D.; Burland, D. M.; Jurich, M.; Lee, V. Y.; Moylan, C. R.; Twieg, R. J.; Thackara, J.; Verbiest, J.; Volksen, W.; Walsh, C. A. In ref 1a and references therein.
30. Jen, A. K.-Y.; Rao, V. P.; Chandrasekhar, J. In ref 1a and references therein.
31. (a) Chou, H.; Suslick K. S. J. Phys. Chem. 1994, 98, 383.
32. (b) Suslick, K. S.; Chen, C.-T.; Meridith, G. R.; Cheng, L.-T.; J. Am. Chem. Soc. 1992, 114, 6928.
33. (a) LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497.
34. (b) Priyadarshy, S.; Therien, M. J.; Beratan D. N. J. Am. Chem. Soc. 1996, 118, 1504.
35. Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Science 1994, 264, 1105.
36. Sen, A.; Ray, P. C.; Das, P. K.; Krishnan, V. J. Phys. Chem. 1996, 100, 19611.
37. Li, D.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 1707.
38. Sliver, S. J.; Tulinsky, A. J. Am. Chem. Soc. 1967, 89, 3331.
39. (a) Varanasi, P. R.; Jen, A. K.-Y.; Chandrasekhar, J.; Namboothiri, I. N. N.; Rathna, A. J. Am. Chem. Soc. 1996, 188, 12443.
40. (b) Albert, I. D. L.; Marks, T. J.; Ratner, M. A. J. Am. Chem. Soc. 1997, 119, 6575.
41. (a) Bacon, A. D.; Zerner, M. C. Theor. Chim. Acta (Berlin) 1979, 53, 21.
42. (b) Ridley, J.; Zerner, M. C. Theor. Chim. Acta (Berlin) 1973, 32, 111.
43. Pople, J. A.; Beveridge, D. L. Approximate Molecular Orbital Theory; McGraw-Hill: New York, 1970.
44. Jespersen, K. K.; Ratner, M. A. Theor. Chim. Acta 1978, 47, 283; J. Chem. Phys. 1976, 65, 1305.
45. Jespersen, K. K.; Ratner, M. A. Theor. Chim. Acta 1978, 47, 283; J. Chem. Phys. 1976, 65, 1305.
46. (a) Albert, I. D. L.; Marks, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 9714.
47. (b) Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J.-L. J. Am. Chem. Soc. 1994, 116, 10703.
48. Marder, S. R.; Perry, J. W.; Bourhill, G.; Gorman, C. B.; Tiemann, B. G.; Mansour, K. Science 1993, 261, 186.
49. Albert, A. Heterocyclic Chemistry; Oxford University Press: New York, 1968.
50. 16
51. (a) Reinhardt, B. A.; Kannan, R.; Bhatt, J. C. SPIE Proc. 1994, 2229, 24.
52. (b) Reinhardt, B. A. SPIE Proc. 1993, 1853, 50.
53. Karna, S., P.; Zhang, Y.; Samoc, M.; Prasad, P. N. Reinhardt, B. A.; Dillard, A. G. J. Chem. Phys. 1993, 99, 9984.
54. (a) Zerner, M. C.; Gouterman, M. Theor. Chim. Acta 1966, 4, 44.
55. (b) Gouterman, M.; Wagmere, G. J. Mol. Spectrosc. 1963, 11, 108.
56. Weiss, C.; Kobayashi, H.; Gouterman, M. J. Mol. Spectrosc. 1963, 16, 415.
57. Kobayashi, H. J. Chem. Phys. 1959, 30, 1362, 1373.
58. (a) Fuhrhop, J.-H. Angew. Chem., Int. Ed. Engl. 1974, 13, 321.
59. (b) Fleischer, E. B. Acc. Chem. Res. 1970, 3, 105.
60. Hoard, J. L. Science 1971, 174, 1295.
61. (a) Janson, T. R.; Katz, J. J. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1979; Vol IV Part B.
62. (b) Scheer, H.; Katz, J. J. In The Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975.
63. Oth, J. F. M.; Baumann, H.; Gilles, J. M.; Schröder, G. J. Am. Chem. Soc. 1972, 94, 3498.
64. Jackman, L. M.; Sternhell, S. Application of NMR Spectroscopy; Pergamon Press: Oxford, 1969.
65. Lloyd, D. The Chemistry of Conjugated Cyclic Compounds. To be or Not to be like Benzene; Wiley: Chichester, 1989.
66. SYBYL is a trademark of Tripos Associates Inc.
67. (a) Ramasesha, S.; Shuai, Z.; Brèdas, J.-L. Chem. Phys. Lett. 1996, 250, 14; 1995, 245, 224.
68. (28) (a) Ramasesha, S.; Shuai, Z.; Brèdas, J.-L. Chem. Phys. Lett. 1996, 250, 14; 1995, 245, 224.
69. (b) Albert, I. D. L.; Morley, J. O.; Pugh, D . J. Chem. Phys. 1995, 102, 237; 1993, 99, 5197.
70. (b) Albert, I. D. L.; Morley, J. O.; Pugh, D . J. Chem. Phys. 1995, 102, 237; 1993, 99, 5197.
71. Soos Z. G.; Ramasesha, S. J. Chem. Phys. 1989, 90, 1067.
72. Svendsen, E. N.; Willand, C. S.; Albrecht, A. C. J. Chem. Phys. 1985, 83, 5760.
73. Ramasesha, S. J. Comput. Chem. 1990, 11, 545.
74. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity. Electronic and Structural Aspects; John Wiley: New York, 1994.
75. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binklet, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Gaussian, Inc.: Pittsburgh, PA, 1992.
76. Kennard, C. H.; Byriel, K. A.; Woon, T. C.; Fairlie, D. P. J. Chem. Soc., Chem. Commun. 1996, 1731.
77. 2 hybridized is correct. In our calculations we have chosen the former resonance structure for the SYBYL optimization.