Electronic structure and molecular conformation in the excited charge transfer singlet states of 9-acridyl and other aryl derivatives of aromatic amines

Journal of the American Chemical Society

Volumn 120, Issue 5, 1998, Pages 1014-1029

  Herbich, Jerzy ^a   Kapturkiewicz, Andrzej ^a  

^a INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; AROMATIC AMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DIPOLE; FLUORESCENCE;

EID: 0032506973     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972474c     Document Type: Article

References (106)

1. Photoinduced electron transfer (Parts A-D); Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988.
2. Kavarnos, G. J. Fundamentals of Photoinduced Electron Transfer; VCH: New York, 1994.
3. E.g., (a) Ulstrup, J.; Jortner, J. J. Chem. Phys. 1975, 63, 4358.
4. (b) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
5. (a) Hush, N. S. Prog. Inorg. Chem. 1967, 8, 391.
6. (b) Hush, N. S. Electrochim. Acta 1968, 13, 1005.
7. (c) Hush, N. S. Coord. Chem. Rev. 1985, 64, 135.
8. Marcus, R. A. J. Phys. Chem. 1989, 93, 3078 and references cited therein.
9. Gould, I. R.; Farid, S. J. Photochem. Photobiol. A: Chem. 1992, 65, 133.
10. Gould, I.R.; Young, R. H.; Moody, R. E.; Farid, S. J. Phys. Chem. 1991, 95, 2068.
11. Gould, I. R.; Noukakis, D.; Gomez-Jahn, L.; Young, R. H.; Goodman, J. L.; Farid, S. Chem. Phys. 1993, 176, 439.
12. Gould, I. R.; Noukakis, D.; Gomez-Jahn, L.; Goodman, J. L.; Farid, S. J. Am. Chem. Soc. 1993, 115, 4405.
13. Gould, I. R.; Young, R. H.; Mueller, L. J.; Farid, S. J. Am. Chem. Soc. 1994, 116, 8176.
14. Gould, I. R.; Young, R. H.; Mueller, L. J.; Albrecht, A. C.; Farid, S. J. Am. Chem. Soc. 1994, 116, 8188.
15. Cortes, J.; Heitele, H.; Jortner, J. J. Phys. Chem. 1994, 98, 2527 and references cited therein.
16. Kapturkiewicz, A.; Herbich, J.; Karpiuk, J.; Nowacki, J. J. Phys. Chem. A 1997, 101, 2332.
17. (a) Oevering, H. Ph.D. Dissertation, University of Amsterdam, Amsterdam, the Netherlands, 1988.
18. (b) Oevering, H.; Verhoeven, J. W.; Paddon-Row, M. N.; Warman, M. J. Tetrahedron 1989, 45, 4751.
19. Oliver, A. M.; Paddon-Row, M. N.; Kroon, J.; Verhoeven, J. W. Chem. Phys. Lett. 1992, 191, 371.
20. Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811.
21. Beratan, D.; Hopfield, J. J. J. Am. Chem. Soc. 1984, 106, 1584.
22. (a) Mataga, N.; Murata, Y. J. Am. Chem. Soc. 1969, 91, 3144.
23. (b) Mataga, N. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic: New York, 1975.
24. (c) Masaki, S.; Okada, T.; Mataga, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1976, 49, 1277.
25. (a) Pasman, P. Ph.D. Dissertation, University of Amsterdam, Amsterdam, the Netherlands, 1980.
26. (b) Pasman, P.; Rob, F.; Verhoeven, J. W. J. Am. Chem. Soc. 1982, 104, 5127.
27. Bixon, M.; Jortner, J.; Verhoeven, J. W. J. Am. Chem. Soc. 1994, 116, 7349 and references cited therein.
28. Verhoeven, J. W.; Scherer, T.; Wegewijs, B.; Hermant, R. M.; Jortner, J.; Bixon, M.; Depaemelaere, S.; De Schryver, F. C. Recl. Trav. Chim. Pays-Bas 1995, 114, 443.
29. Herbich, J.; Kapturkiewicz, A. Chem. Phys. Lett. 1997, 273, 8.
30. (a) Rettig, W.; Zander, M. Ber. Bunsen-Ges. Phys. Chem. 1983, 87, 143.
31. (b) Mataga, N.; Nishikawa, S.; Okada, T. Chem. Phys. Lett. 1996, 257, 327.
32. Dobkowski, J.; Grabowski, Z. R.; Paeplow B.; Rettig, W.; Koch, K. H.; Müllen, K.; Lapouyade, R. New J. Chem. 1994, 18, 525 and references cited therein.
33. (a) Okada, T.; Fujita, T.; Kubota, M.; Masaki, S.; Mataga, N.; Ide, R.; Sakata, Y.; Misumi, S. Chem. Phys. Lett. 1972, 14, 563.
34. (b) Okada, T.; Fujita, T.; Mataga, N. Z. Physik. Chem. NF 1976, 101, 57.
35. (a) Grabowski, Z. R.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J.; Baumann, W. NouV. J. Chim. 1979, 3, 443.
36. (b) Siemiarczuk, A.; Grabowski, Z. R.; Krówczynski, A.; Asher, M.; Ottolenghi, M. Chem. Phys. Lett. 1977, 51, 315.
37. (c) Siemiarczuk, A.; Koput, J.; Pohorille, A. Z. Naturforsch. 1982, 37a, 598.
38. Tominaga, K.; Walker, G. C.; Jarzeüba, W.; Barbara, P. F. J. Phys. Chem. 1991, 95, 10475.
39. (a) Herbich, J.; Kapturkiewicz, A. Chem. Phys. 1991, 158, 143.
40. (b) Herbich, J.; Kapturkiewicz, A. Chem. Phys. 1993, 170, 221.
41. Onkelinx, A.; De Schryver, F. C.; Viaene, L.; Van der Auweraer, M.; Iwai, K.; Yamamoto, M.; Ichikawa, M.; Masuhara, H.; Maus, M.; Rettig, W. J. Am. Chem. Soc. 1996, 118, 2892.
42. Van Damme, W.; Hofkens, J.; De Schryver, F. C.; Ryan, T. G.; Rettig, W.; Klock, A. Tetrahedron 1989, 45, 4693.
43. Herbich, J.; Waluk, J. Chem. Phys. 1994, 188, 247.
44. Rettig, W.; Zander, M. Chem. Phys. Lett. 1982, 87, 229.
45. Murrell, J. N. J. Am. Chem. Soc. 1959, 81, 5037.
46. Mulliken, R. S.; Person, W. B. In Molecular Complexes: A Lecture and Reprint Volume; Wiley: New York, 1969.
47. Beens, H.; Weller, A. In Organic Molecular Photophysics; Birks, J. B., Ed.; Wiley: New York, 1975; p 159.
48. Van der Auweraer, M.; Swinnen, A. M.; De Schryver, F. C. J. Chem. Phys. 1982, 77, 4110.
49. Okada, T.; Mataga, N.; Baumann, W.; Siemiarczuk, A. J. Phys. Chem. 1987, 91, 4490.
50. Herbich, J.; Kapturkiewicz, A.; Nowacki, J. Chem. Phys. Lett. 1996, 262, 633.
51. Kapturkiewicz, A.; Grabowski, Z. R.; Jasny, J. J. Electroanal. Chem. 1990, 279, 55.
52. (a) Kapturkiewicz, A. J. Electroanal. Chem. 1991, 302, 131.
53. (b) Kapturkiewicz, A. Z. Physik. Chem. 1991, 170, 87.
54. Kapturkiewicz, A. Chem. Phys. 1992, 166, 259.
55. Kapturkiewicz, A. J. Electroanal. Chem. 1993, 348, 283.
56. Kapturkiewicz, A.; Herbich, J.; Nowacki, J. Chem. Phys. Lett. 1997, 275, 355.
57. Baumann, W.; Raber, W. Unpublished results.
58. Ullmann, F.; Bader, W.; Labhardt, H. Ber. Deut. Chem. Ges. 1907, 40, 4795.
59. Reichardt, C. SolVent Effects in Organic Chemistry; Verlag: New York, 1979.
60. Jasny, J. J. Lumin. 1978, 17, 143.
61. (a) Velapoldi, R. A. National Bureau of Standards 378, Proc. Conf. NBS, Gaithersburg, ms 1972; p 231.
62. (b) Kubin, R. F.; Fletcher, A. N. J. Lumin. 1982, 27, 455.
63. (c) Karstens, T.; Kobs, K. J. Phys. Chem. 1980, 84, 1871.
64. (d) Cook, M. J.; Lewis, A. P.; McAuliffe, G. S. G.; Skarda, V.; Thomson, A. J. J. Chem. Soc., Perkin Trans II. 1984, 1293.
65. Karpiuk, J.; Grabowski, Z. R. Chem. Phys. Lett. 1989, 160, 451.
66. Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 11, 431.
67. Steiner, R. P.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6861.
68. (a) Zanker, V.; Schmid, W. Chem. Ber. 1957, 90, 2253.
69. (b) Zanker, V.; Schiefele, G. Z. Elektrochem. 1958, 62, 86.
70. (c) Zanker, V.; Schmid, W. Chem. Ber. 1959, 92, 615.
71. (d) Perkampus, H.-H.; Kortüm, K. Z. Physik. Chem. NF, 1967, 56, 73.
72. (e) Seiffert W.; Limbach, H.; Zanker, V.; Mantsch, H. H. Tetrahedron 1970, 26, 2663.
73. (f) Inoue, H.; Hoshi, T.; Masamoto, T.; Shiraishi, J.; Tanizaki, Y. Ber. Bunsen-Ges. Phys. Chem. 1971, 75, 441.
74. Wagner, R. W.; Hochmann, P.; Al-Bayoumi, M. A. J. Mol. Spectr. 1975, 54, 167.
75. Böttcher, C. J. F. In Theory of Electric Polarization; Van Belle, O. C., Bordewijk, P., Rip, A., Eds.; Elsevier: Amsterdam, 1973; Vol. 1.
76. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
77. (a) Lippert, E. Z. Naturforsch. 1955, 10a, 541.
78. (b) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1955, 28, 690.
79. Liptay, W. In Excited States; Lim, E. C., Ed.: Academic Press: New York, 1974; p 129.
80. (a) Grampp, G.; Jaenicke, W. Ber. Bunsen-Ges. Phys. Chem. 1991, 95, 904.
81. (b) Fawcett, W.R.; Opatto, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2131.
82. (a) Allinger, N. L. Adv. Phys. Org. Chem. 1976, 13, 1.
83. Baumann, W; Petzke, F.; Loosen, K.-D. Z. Naturforsch. 1979, 34a, 1070.
84. Baumann, W. Z. Naturforsch. 1981, 36a, 868.
85. (c) Detzer, N.; Baumann, W.; Schwager, B.; Fröhling, J.-C.; Brittinger, C. Z. Naturforsch. 1987, 42a, 395.
86. Herbich, J.; Dobkowski, J.; Rullière, C.; Nowacki, J. J. Lumin. 1989, 44, 87.
87. McRae, E. G. J. Phys. Chem. 1957, 61, 562.
88. Birks, J. B. In Photophysics of Aromatic Molecules; Wiley: New York, 1978; p 51.
89. Michl, J.; Thulstrup, E. W. In Spectroscopy with Polarized Light; VCH: New York, 1986; pp 28 and 75.
90. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1971; p 159.
91. Dogonadze, R. R.; Kuznetsov, A. M.; Marsagishvili, T. A. Electrochim. Acta 1980, 25, 1.
92. Bader, J. S.; Berne, B.J. J. Chem. Phys. 1996, 104, 1293.
93. Marcus, R. A. J. Chem. Phys. 1965, 43, 679.
94. (a) Matyushov, D. V.; Schmid, R. J. Chem. Phys. 1995, 103, 2034.
95. (b) Matyushov, D. V. Chem. Phys. 1996, 211, 47.
96. (c) Matyushov, D. V.; Schmid, R.; Ladanyi, B. M. J. Phys. Chem. B 1997, 101, 1035.
97. Efrima, S.; Bixon, M. Chem. Phys. Lett. 1974, 25, 341.
98. Wiessner, A.; Hüttmann, G.; Kühnle, W.; Staerk, H. J. Phys. Chem. 1995, 99, 14923.
99. (a) Kolc, J.; Thulstrup, E.W.; Michl, J. J. Am. Chem. Soc. 1974, 96, 7188.
100. (b) Dalgaard, G.P.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6867.
101. (a) Vasák, M.; Whipple, M. R.; Berg, A.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6872.
102. (b) Waluk, J. W.; Michl, J. Anal. Chem. 1981, 53, 236.
103. (a) Vasák, M.; Whipple, M. R.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6838.
104. (b) Whipple, M. R.; Vasák, M.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6844.
105. Vasák, M.; Whipple, M. R.; Michl, J. J. Am. Chem. Soc. 1978, 100, 6867.
106. Tseng, J. C. C.; Huang, S.; Singer, L. A. Chem. Phys. Lett. 1988, 153, 401.