One- and two-photon spectroscopy of donor-acceptor-donor distyrylbenzene derivatives: Effect of cyano substitution and distortion from planarity

Journal of Physical Chemistry A

Volumn 106, Issue 47, 2002, Pages 11470-11480

  Pond, Stephanie J K ^a   Rumi, Mariacristina ^a   Levin, Michael D ^b   Parker, Timothy C ^a   Beljonne, David ^c   Day, Michael W ^b   Brédas, Jean Lue ^a,c   Marder, Seth R ^a,d   Perry, Joseph W ^a,d  

^a University of Arizona   (United States)

^b California Institute of Technology   (United States)

^c UNIVERSITY OF MONS   (Belgium)

^d UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR DYNAMICS; PHOTONS; SPECTROSCOPIC ANALYSIS; SUBSTITUTION REACTIONS;

TWO PHOTON SPECTROSCOPY;

BENZENE;

EID: 0037191797     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0267104     Document Type: Article

References (63)

1. Denk, W.; Strickler, J.H.; Webb, W.W. Science 1990, 248, 73-76.
2. Fisher, W.G.; Partridge, W.P., Jr.; Dees, C.; Wachter, E.A. Photochem. Photobiol. 1997. 66, 141-155.
3. Spangler, C.W. J. Mater. Chem. 1999, 9, 2013-2020.
4. Wu, E.S.; Strickler, J.H.; Harrell, W.R.; Webb, W.W. Proc. SPIE 1992, 1674, 776-782.
5. Maruo, S.; Nakamura, O.; Kawata, S. Opt. Lett. 1997, 22, 132- 134.
6. Cumpston, B.H.; Ananthavel, S.P.; Barlow, S.; Dyer, D.L.; Ehrlich, J.E.; Erskine, L.L.; Heikal, A.A.; Kuebler, S.M.; Lee, I.-Y.S.; McCord-Maughon, D.; Qin, J.; Röckel, H.; Rumi, M.; Wu, X.-L.; Marder, S.R.; Perry, J.W. Nature 1999, 398, 51-54.
7. Zhou, W.; Kuebler, S.M.; Braun, K.L.; Yu, T.; Cammack, J.K.; Ober, C.K.; Perry, J.W.; Marder, S.R. Science 2002, 296, 1106-1109.
8. 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.
9. Rumi, M.; Ehrlich, J.E.; Heikal, A.A.; Perry, J.W.; Barlow, S.; Hu, Z.; McCord-Maughon, D.; Parker, T.C.; Röckel, H.; Thayumanavan, S.; Marder, S.R.; Beljonne, D.; Brédas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500-9510.
10. 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.
11. Ventelon, L.; Moreaux, L.; Mertz, J.; Blanchard-Desce, M. Chem. Commun. 1999, 2055-2056.
12. Zojer, E.; Beljonne, D.; Kogej, T.; Vogel, H.; Marder, S.R.; Perry, J.W.; Brédas, J.L. J. Chem. Phys. 2002, 116, 3646-3658.
13. Kotler, Z.; Segal, J.; Sigalov, M.; Ben-Asuly, A.; Khodorkovsky, V. Synth. Met. 2000, 115, 269-273.
14. Morel, Y.; Irimia, A.; Najechalski, P.; Kervella, Y.; Stephan, O.; Baldeck, P.L.; Andraud, C. J. Chem. Phys. 2001, 114, 5391-5396.
15. Najechalski, P.; Morel, Y.; Stéphan, O.; Baldeck, P.L. Chem. Phys. Lett. 2001, 343, 44-48.
16. Cho, B.R.; Son, K.H.; Lee, S.H.; Song, Y.-S.; Lee, Y.-K.; Jeon, S.-J.; Choi, J.H.; Lee, H.; Cho, M. J. Am. Chem. Soc. 2001, 123, 10039-10045.
17. Beljonne, D.; Wenseleers, W.; Zojer, E.; Shuai, Z.; Vogel, H.; Pond, S.J.K.; Perry, J.W.; Marder, S.R.; Brédas, J.L. Adv. Funct. Mater. 2002, 12, 631-641.
18. Chung, S.-J.; Kim, K.-S.; Lin, T.-C.; He, G.S.; Swiatkiewicz, J.; Prasad, P.N. J. Phys. Chem. B 1999, 103, 10741-10745.
19. Drobizhev, M.; Karotki, A.; Rebane, A.; Spangler, C.W. Opt. Lett. 2001, 26, 1081-1083.
20. Chen, D.; Winokur, M.J.; Masse, M.A.; Karazs, F.E. Polymer 1992, 33, 3116-3122.
21. Mao, G.; Fischer, J.E.; Karasz, F.E.; Winokur, M.J. J. Chem. Phys. 1993, 98, 712-716.
22. van Hutten, P.F.; Wildeman, J.; Meetsma, A.; Hadziioannou, G. J. Am. Chem. Soc. 1999, 121, 5910-5918.
23. Hohloch, M.; Maichle-Mössmer, C.; Hanack, M. Chem. Mater. 1998, 10, 1327-1332.
24. Bartholomew, G.P.; Bazan, G.C.; Bu, X.; Lachicotte, R. J. Chem. Mater. 2000, 12, 1422-1430.
25. Gill, R.E.; Hilberer, A.; van Hutten, P.F.; Berentschot, G.; Werts, M.P.L.; Meetsma, A.; Wittmann, J.-C.; Hadziioannou, G. Synth. Met. 1997, 84, 637-638.
26. Fahlman, M.; Brédas, J.L. Synth. Met. 1996, 78, 39-46.
27. Pati, S.K.; Marks, T.J.; Ratner, M.A. J. Am. Chem. Soc. 2001, 123, 7287-7291.
28. Poulsen, T.D.; Frederiksen, P.K.; Jørgensen, M.; Mikkelsen, K.V.; Ogilby, P.R. J. Phys. Chem. A 2001, 105, 11488-11495.
29. Wenseleers, W.; Stellacci, F.; Meyer-Friedrichsen, T.; Mangel, T.; Bauer, C.A.; Pond, S.J.K.; Marder, S.R.; Perry, J.W. J. Phys. Chem. B 2002, 106, 6853-6863.
30. Xiao, Y.; Yu, W.-L.; Chua, S.-J.; Huang, W. Chem. Eur. J. 2000, 6, 1318-1321.
31. Pinto, M.R.; Hu, B.; Karasz, F.E.; Akcelrud, L. Polymer 2000, 41, 2603-2611.
32. Baker, T.N., III; Doherty, W.P., Jr.; Kelley, W.S.; Newmeyer, W.; Rogers, J.E., Jr.; Spalding, R.,E.; Walter, R.I. J. Org. Chem. 1965, 30, 3714-3718.
33. Sheldrick, G.M. Acta Crystallogr. A 1990, 46, 467-473.
34. Berlman, I.B. Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed.; Academic Press: New York, 1971.
35. O'Connor, D.V.; Phillips, D. Time-correlated Single Photon Counting; Academic Press: London, 1984.
36. Khundkar, L.R.; Perry, J.W.; Hanson, J.E.; Dervan, P.B. J. Am. Chem. Soc. 1994, 116, 9700-9709.
37. Xu, C.; Webb, W.W. J. Opt. Soc. Am. B 1996, 13, 481-491.
38. Fisher, W.G.; Wachter, E.A.; Lytle, F.E.; Armas, M.; Seaton, C. Appl. Spectrosc. 1998, 52, 536-545.
39. Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
40. Ridley, J.; Zerner, M. Theor. Chim. Acta 1973, 32, 111-134.
41. Orr, B.J.; Ward, J.F. Mol. Phys. 1971, 20, 513-526.
42. 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.
43. Herzberg, G. Molecular Spectra and Molecular Structure.I. Spectra of Diatomic Molecules, 2nd ed.; Van Nostrand Reinhold Co.: New York, 1950.
44. Coon, J.B.; DeWames, R.E.; Loyd, C.M. J. Mol. Spectrosc. 1962, 8, 285-299.
45. Katriel, J. J. Phys. B: Atom. Mol. Phys. 1970, 3, 1315-1320.
46. Cornil, J.; Beljonne, D.; Shuai, Z.; Hagler, T.W.; Campbell, I.; Bradley, D.D.C.; Brédas, J.L.; Spangler, C.W.; Müllen, K. Chem. Phys. Lett. 1995, 247, 425-432.
47. Innes, K.K. In Excited States; Lim, E.C., Ed.; Academic Press: New York, 1975; Vol. 2; pp 1-32.
48. Cornil, J.; Beljonne, D.; Heller, C.M.; Campbell, I.H.; Laurich, B.K.; Smith, D.L.; Bradley, D.D.C.; Müllen, K.; Brédas, J.L. Chem. Phys. Lett. 1997, 278, 139-145.
49. Oelkrug, D.; Tompert, A.; Gierschner, J.; Egelhaaf, H.-J.; Hanack, M.; Hohloch, M.; Steinhuber, E. J. Phys. Chem. B 1998, 102, 1902-1907.
50. de Souza, M.M.; Rumbles, G.; Gould, I.R.; Amer, H.; Samuel, I.D.W.; Moratti, S.C.; Holmes, A.B. Synth. Met. 2000, 111-112, 539-543.
51. Ichino, Y.; Ni, J.P.; Ueda, Y.; Wang, D.K. Synth. Met. 2001, 116, 223-227.
52. Birckner, E.; Grummt, U.-W.; Rost, H.; Hartmann, A.; Pfeiffer, S.; Tillmann, H.; Hörhold, H.-H. J. Fluoresc. 1998, 8, 73-80.
53. Birge, R.R. In Ultrasensitive Laser Spectroscopy; Kliger, D.S., Ed.; Academic Press: New York, 1983; pp 109-174.
54. Karabunarliev, S.; Baumgarten, M.; Bittner, E.R.; Müllen, K. J. Chem. Phys. 2000, 113, 11372-11381.
55. Karabunarliev, S.; Baumgarten, M.; Müllen, K. J. Phys. Chem. A 2000, 104, 8236-8243.
56. Tian, B.; Zerbi, G.; Schenk, R.; Müllen, K. J. Chem. Phys. 1991, 95, 3191-3197.
57. Demas, J.N. Excited Stare Lifetime Measurements; Academic Press: New York, 1983.
58. van Hutten, P.F.; Krasnikov, V.V.; Hadziioannou, G. Acc. Chem. Res. 1999, 32, 257-265.
59. Beljonne, D.; Shuai, Z.; Pourtois, G.; Brédas, J.L. J. Phys. Chem. A 2001, 105, 3899-3907.
60. Liu, M.S.; Jiang, X.; Jen, A.K.-Y. Mater. Res. Soc. Symp. Proc. 2000, 598, BB5.53.1-BB5.53.8.
61. 8 (δ = 1940 GM with nanosecond pulses and 3670 GM using femtosecond pulses) and reflects the most recent measurements performed in our laboratory.
62. Kogej, T.; Beljonne, D.; Meyers, F.; Perry, J.W.; Marder, S.R.; Brédas, J.L. Chem. Phys. Lett. 1998, 298, 1-6.
63. 1c′ and 3c′ are thus acting as model compounds for 2 and 4, although the effects of the different substituents on the amino end groups was not accounted for.