Structure - Property relationships for two-photon absorbing chromophores: Bis-donor diphenylpolyene and bis(styryl)benzene derivatives

Journal of the American Chemical Society

Volumn 122, Issue 39, 2000, Pages 9500-9510

  Rumi, Mariacristina ^a   Ehrlich, Jeffrey E ^b   Heikal, Ahmed A ^b   Perry, Joseph W ^a,c   Barlow, Stephen ^b   Hu, Zhongying ^b   McCord Maughon, Dianne ^b   Parker, Timothy C ^a   Röckel, Harald ^b   Thayumanavan, Sankaran ^a,b   Marder, Seth R ^a,c   Beljonne, David ^d   Brédas, Jean Luc ^a,d  

^a University of Arizona ^*  (United States)

^b California Institute of Technology ^*  (United States)

^c UNIVERSITY OF ARIZONA   (United States)

^d UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BIS(STYRYL)BENZENE; DIPHENYLPOLYENE; POLYENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIPOLE; LIGHT ABSORPTION; PHOTON; QUANTUM MECHANICS;

EID: 17544392421     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994497s     Document Type: Article

References (50)

1. Bhawalkar, J. D.; He, G. S.; Prasad, P. N. Rep. Prog. Phys. 1996, 59, 1041-1070.
2. Perry, J. W.; Mansour, K.; Lee, I.-Y. S.; Wu, X.-L.; Bedworth, P. V.; Cheng, C-T.; Ng, D.; Marder, S. R.; Miles, P.; Wada, T.; Tian, M.; Sasabe, H. Science 1996, 273, 1533-1536.
3. Ehrlich, J. E.; Wu, X.-L.; Lee, I.-Y. S.; Hu, Z.-Y.; Röckel, H.; Marder, S. R.; Perry, J. W. In Materials Research Society Symposium Proceedings, Materials for Optical Limiting II, Vol. 479; Sutherland, R., Patcher, R., Hood, P., Hagan, D., Lewis, K., Perry, J. W., Eds.; MRS: Pittsburgh, 1997; pp 9-15.
4. Denk, W.; Strickler, J. H.; Webb, W. W. Science 1990, 248, 73-76.
5. Strickler, J. H.; Webb, W. W. SPIE Proceedings 1990, 1398, 107-118.
6. Maruo, S.; Nakamura, O.; Kawata, S. Opt. Lett. 1997, 22, 132-134.
7. Albota, M.; Beljonne, D.; Brédas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Röckel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653-1656.
8. Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863-1874.
9. Hudson, B.; Kohler, B. Annu. Rev. Phys. Chem. 1974, 25, 437-460.
10. Hudson, B. S.; Kohler, B. E.; Schulten, K. In Excited States, Vol. 6; Lim, E. C., Ed.; Academic Press: New York, 1982; pp 1-95.
11. Xu, C.; Webb, W. W. J. Opt. Soc. Am. B 1996, 13, 481-491.
12. 11 at 690 nm.
13. Khundkar, L. R.; Perry, J. W.; Hanson, J. E.; Dervan, P. B. J. Am. Chem. Soc. 1994, 116, 9700-9709.
14. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
15. Ridley, J.; Zerner, M. Theor. Chim. Acta, 1973, 32, 111-134.
16. Dick, B.; Hochstrasser, R. M.; Trommsdorff, H. P. Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 2; Chemla, D. S., Zyss, J., Eds.; Academic Press: Orlando, 1987; pp 159-212.
17. Loudon, R. The Quantum Theory of Light; Oxford University Press; London, 1973; Chapter 5, pp 81-119.
18. Xu, C.; Webb, W. W. In Topics in Fluorescence Spectroscopy, Vol. 5 (Nonlinear and Two-Photon-Induced Fluorescence); Lakowicz, J., Ed.; Plenum Press: New York, 1997; pp 471-540.
19. Perry, J. W.; Barlow, S.; Ehrlich, J. E.; Heikal, A. A.; Hu, Z.-Y.; Lee, I.-Y. S.; Mansour, K.; Marder, S. R.; Röckel, H.; Rumi, M.; Thayumanavan, S.; Wu, X. L. Nonlinear Opt. 1999, 21, 225-243.
20. Ehrlich, J. E.; Wu, X.-L.; Lee, I.-Y. S.; Hu. Z.-Y.; Röckel, H.; Marder, S. R.; Perry, J. W. Opt. Lett. 1997, 22, 1843-1845.
21. Anderson, R. M. J.; Holtom, G. R.; McClain, W. M. J. Chem. Phys. 1979, 70, 4310-4315.
22. McConnell, H. M. J. Chem. Phys. 1961, 35, 508-515.
23. Beljonne, D.; Meyers, F.; Brédas, J. L. Synth. Met. 1996, 80, 211-222.
24. Brédas, J.-L., unpublished results.
25. Kohler, B. E. J. Chem. Phys. 1990, 93, 5838-5842.
26. Hudson, B. S.; Kohler, B. E. J. Chem. Phys. 1973, 59, 4984-5002.
27. Itoh, T.; Kohler, B. E. J. Phys. Chem. 1987, 91, 1760-1764.
28. Hudson, B. S.; Kohler, B. E. Chem. Phys. Lett. 1972, 14, 299-304.
29. Buma, W. J.; Kohler, B. E.; Song, K. J. Chem. Phys. 1990, 92, 4622-4623.
30. Itoh, T.; Kohler, B. E.; Spangler, C. W. Spectrochimica Acta 1994, 50A, 2261-2263.
31. Bachilo, S. M.; Spangler, C. W.; Gillbro, T. Chem. Phys. Lett. 1998, 283, 235-242.
32. Kohler, B. E.; Spangler, C.; Westerfield, C. J. Chem. Phys. 1988, 89, 5422-5428.
33. Birge, R. R. In Ultrasensitive Laser Spectroscopy; Kliger, D. S., Ed.; Academic Press: New York, 1983; pp 109-174.
34. Swofford, R. L.; McClain, W. M. J. Chem. Phys. 1973, 59, 5740-5741.
35. Perry, J. W., unpublished results.
36. Sutherland, R. L. Handbook of Nonlinear Optics; Marcel Dekker: New York, 1996; Chapter 9, pp 497-548.
37. Butcher, P. N.; Cotter, D. The Elements of Nonlinear Optics; Cambridge University Press: Cambridge, 1990.
38. Kogej, T.; Beljonne, D.; Meyers, F.; Perry, J. W.; Marder, S. R.; Brédas, J. L. Chem. Phys. Lett. 1998, 298, 1-6.
39. Mulliken, R. S. J. Chem. Phys. 1939, 7, 14-20.
40. Herzberg, G. Molecular spectra and molecular structure. I. Spectra of diatomic molecules; Van Nostrand Reinhold Company: New York, 1950; pp 381-385.
41. A more complete treatment that accounts for the Franck-Condon distribution and the homogeneous and inhomogeneous broadenings will be considered in future work.
42. (a) Becker, P. C.; Fragnito, H. L.; Bigot, J. Y.; Brito Cruz, C. H.; Fork, R. L.; Shank, C. V. Phys. Rev. Lett. 1989, 63, 505-507.
43. (b) Bigot, J. Y.; Portella, M. T.; Schoenlein, R. W.; Bardeen C. J.; Migus, A.; Shank, C. V. Phys. Rev. Lett. 1991, 66, 1138-1141.
44. (c) Bardeen C. J.; Shank, C. V. Chem. Phys. Lett. 1993, 203, 535-539.
45. (a) Cong, P.; Deuel, H. P.; Simon, J. D. Chem. Phys. Lett. 1993, 212, 367-373.
46. (b) Cong, P.; Deuel, H. P.; Yan, Y.-J.; Simon, J. D. J. Luminesc. 1994, 60-61, 699-702.
47. Joo, T.; Albrecht, A. C. Chem. Phys. 1993, 176, 233-247.
48. Lawless, M. K.; Mathies, R. A. J. Chem. Phys. 1992, 96, 8037-8045.
49. Kummrow, A.; Lau, A.; Lenz, K. Phys. Rev. B 1997, 55, 2310-2320.
50. Kohler, B. E. Synth. Met. 1991, 41-43, 1215-1223.