Intramolecular excimer formation in short- and long-chainlength di(9- anthryl) bichromophoric compounds and relation to ground state properties

New Journal of Chemistry

Volumn 23, Issue 4, 1999, Pages 453-460

  Rettig, Wolfgang ^a   Paeplow, Barbara ^b   Herbst, Heinz ^c   Müllen, Klaus ^c,d   Desvergne, Jean Pierre ^e   Bouas Laurent, Henri ^e  

^a HUMBOLDT UNIVERSITY   (Germany)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

^d MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^e CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DI(9 ANTHRYL)PROPANE; 9 DECYLANTHRACENE; 9,9',10,10' TETRAHYDRO 1,3 DI(9 ANTHRYL)PROPANE; ANTHRACENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHROMATOPHORE; CONFORMATION; CRYSTAL STRUCTURE; FLUORESCENCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032808938     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809363f     Document Type: Article

References (105)

1. (a) T. Förster and K. Kasper, Z. Phys. Chem. (N.F.), 1954, 1, 275;
2. (b) T. Förster, Angew. Chem., Int. Ed. Engl., 1969, 8, 333;
3. (c) J. B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, New York, 1970, ch. 7;
4. (d) J. B. Birks, Rep. Prog. Phys., 1975, 38, 903.
5. (a) W. Klöpffer, in Organic Molecular Photophysics, ed. J. B. Birks, J. Wiley, New York, 1973, vol. 1, ch. 7;
6. G. E. Johnson, J. Chem. Phys., 1975, 63, 4047;
7. (b) J. Vandendriessche, R. Goedeweeck, P. Collart and F. C. De Schryver, in Photophysical and Photochemical Tools in Polymer Science, ed. A. Winnik, Nato ASI Series, Series C, Kluwer, Dordrecht, 1986, p. 225;
8. (c) M. Itoh and Y. Fujiwara, Bull. Chem. Soc. Jpn., 1984, 57, 2261;
9. (d) M. F. Sonnenscheim and R. G. Weiss, J. Phys. Chem., 1988, 92, 6828;
10. (e) N. J. Turro, M. Aikawa and A. Yekta, J. Am. Chem. Soc., 1979, 101, 772.
11. (a) M. Goldenberg, J. Emert and H. Morawetz, J. Am. Chem. Soc., 1978, 100, 7171;
12. (b) H. Yoshizawa, K. Ashikaga and M. Yamamoto, Polymer, 1989, 30, 534.
13. (a) F. Hirayama, J. Chem. Phys., 1965, 42, 3163;
14. (b) K. A. Zachariasse, W. Kühnle and A. Weller, Chem. Phys. Lett., 1978, 59, 375.
15. (a) E. A. Chandross and C. J. Dempster, J. Am. Chem. Soc., 1970, 92, 3586;
16. (b) P. Avouris, J. Kordas and A. El-Bayoumi, Chem. Phys. Lett., 1974, 26, 373;
17. (c) R. S. Davidson and T. D. Whelan, J. Chem. Soc., Chem. Commun., 1977, 361;
18. (d) K. Demeyer, M. Van der Auweraer, L. Aertz and F. C. De Schryver, J. Chim. Phys., 1980, 77, 493;
19. (e) P. C. Subudhi and E. C. Lim, Chem. Phys. Lett., 1976, 44, 479; B. T. Lim, S. H. Lin and E. C. Lim, J. Chem. Phys., 1983, 78, 1112;
20. (e) P. C. Subudhi and E. C. Lim, Chem. Phys. Lett., 1976, 44, 479; B. T. Lim, S. H. Lin and E. C. Lim, J. Chem. Phys., 1983, 78, 1112;
21. (f) S. Ito, M. Yamamoto and Y. Nishijima, Bull. Chem. Soc. Jpn., 1982, 55, 363;
22. ibid., 1984, 57, 3295;
23. (g) T. Ikeda, B. Lee, S. Kurihara, S. Tazuke, S. Ito and M. Yamamoto, J. Am. Chem. Soc., 1988, 110, 8299.
24. (a) K. A. Zachariasse and W. Kühnle, Z. Phys. Chem. (N.F.), 1976, 101, 267;
25. (b) K. A. Zachariasse, R. Busse, G. Duveneck and W. Kühnle, J. Photochem., 1985, 28, 237;
26. (c) P. Reynders, H. Dreeskamp, W. Kühnle and K. Zachariasse, J. Phys. Chem., 1987, 91, 3982;
27. (d) A. Siemiarczuk and W. R. Ware, Chem. Phys. Lett., 1987, 140, 277;
28. (e) K. Hara and H. Yano, J. Am. Chem. Soc., 1988, 110, 1911;
29. (f) P. Reynders, W. Kühnle and A. Zachariasse, J. Am. Chem. Soc., 1990, 112, 3929.
30. (a) R. Livingston and K. S. Wei, J. Am. Chem. Soc., 1967, 89, 3098;
31. (b) F. C. De Schryver, M. De Brackeleire, S. Toppet and M. Schoor, Tetrahedron Lett., 1973, 1253;
32. (c) J. Ferguson, M. Morita and M. Puza, Chem. Phys. Lett., 1976, 42, 288; ibid., 1977, 49, 265;
33. (c) J. Ferguson, M. Morita and M. Puza, Chem. Phys. Lett., 1976, 42, 288; ibid., 1977, 49, 265;
34. (d) M. Daney, R. Lapouyade, G. Felix and H. Bouas-Laurent, F.P. Appl. 75/18, 558, June 13, 1975; Chem. Abstr., 1977, 87, 134837h;
35. (d) M. Daney, R. Lapouyade, G. Felix and H. Bouas-Laurent, F.P. Appl. 75/18, 558, June 13, 1975; Chem. Abstr., 1977, 87, 134837h;
36. (e) T. Hayashi, N. Mataga, Y. Sakata, S. Misumi, M. Morita and J. Tanaka, J. Am. Chem. Soc., 1976, 98, 5910;
37. (f) F. C. De Schryver, N. Boens, J. Huybrechts, J. Daemen and M. De Brackeleire, Pure Appl. Chem., 1977, 49, 237;
38. (g) W. R. Bergmark, G. Jones II, T. E. Reinhardt and A. M. Halpern, J. Am. Chem. Soc., 1978, 100, 6665;
39. (h) B. F. Andersen, J. Ferguson, M. Morita and G. B. Robertson, J. Am. Chem. Soc., 1979, 101, 1832;
40. (i) T. Kabayashi, S. Nagakura and M. Swarcz, Chem. Phys., 1979, 39, 105;
41. (j) A. Castellan, J.-P. Desvergne and H. Bouas-Laurent, Chem. Phys. Lett., 1980, 76, 390; J. Ferguson, ibid., 1980, 76, 398;
42. (j) A. Castellan, J.-P. Desvergne and H. Bouas-Laurent, Chem. Phys. Lett., 1980, 76, 390; J. Ferguson, ibid., 1980, 76, 398;
43. (k) M. Itoh, K. Fuke and S. Kobayashi, J. Chem. Phys., 1980, 72, 1417;
44. (l) H. D. Becker, T. Elebring and K. Sandros, J. Org. Chem., 1982, 47, 1064;
45. (m) A. Castellan, J.-P. Desvergne, R. Lesclaux and J.-C. Soulignac, Chem. Phys. Lett., 1984, 106, 117;
46. (n) J.-P. Desvergne, N. Bitit, A. Castellan, M. Webb and H. Bouas-Laurent, J. Chem. Soc., Perkin Trans. 2, 1988, 1885;
47. (o) T. Ikeda, B. Lee, S. Tazuke and A. Tanaka, J. Am. Chem. Soc., 1990, 112, 4650;
48. (p) G. D. Scholes, K. P. Ghiggino and G. J. Wilson, Chem. Phys., 1991, 155, 127;
49. (q) A. Dunand, J. Ferguson, M. Puza and G. B. Robertson, Chem. Phys., 1980, 53, 225; J. Am. Chem. Soc., 1980, 102, 3524;
50. (q) A. Dunand, J. Ferguson, M. Puza and G. B. Robertson, Chem. Phys., 1980, 53, 225; J. Am. Chem. Soc., 1980, 102, 3524;
51. (r) J. Ferguson, Chem. Phys. Lett., 1981, 79, 198.
52. (a) H. Bouas-Laurent, A. Castellan and J.-P. Desvergne, Pure Appl. Chem., 1980, 52, 2633;
53. (b) H. Bouas-Laurent and J.-P. Desvergne, in Photochromism, Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, p. 561.
54. (a) H. D. Becker, in Advances in Photochemistry, ed. D. H. Volman, G. S. Hammond and K. Gollnick, Interscience, New York, 1990, vol. 15, p. 139;
55. (b) H. D. Becker, Chem. Rev., 1993, 93, 145;
56. (c) H. D. Becker, V. Langer, J. Sieler and H. C. Becker, J. Org. Chem., 1992, 57, 1883.
57. (a) T. Hayashi, T. Suzuki, N. Mataga, Y. Sakata and S. Misumi, Chem. Phys. Lett., 1976, 38, 599; J. Phys. Chem., 1977, 81, 420;
58. (a) T. Hayashi, T. Suzuki, N. Mataga, Y. Sakata and S. Misumi, Chem. Phys. Lett., 1976, 38, 599; J. Phys. Chem., 1977, 81, 420;
59. (b) H. Yao, T. Okado and N. Mataga, J. Phys. Chem., 1989, 93, 7388.
60. R. J. Visser, P. C. M. Weisenborn, P. J. M. van Kan, B. H. Huizer, C. A. G. O. Varma, J. M. Warman and M. P. de Haas, J. Chem. Soc., Faraday Trans. 2, 1985, 81, 689.
61. W. Rettig, Angew. Chem., Int. Ed. Engl., 1986, 25, 971.
62. A. Subaric-Leitis, C. Monte, A. Roggan, W. Rettig, P. Zimmermann and J. Heinze, J. Chem. Phys., 1990, 93, 4543.
63. F. Schneider and E. Lippert, Ber. Bunsen-Ges. Phys. Chem., 1968, 72, 1155.
64. F. Schneider and E. Lippert, Ber. Bunsen-Ges. Phys. Chem., 1970, 74, 624.
65. H. Beens and A. Weller, Chem. Phys. Lett., 1969, 3, 666.
66. N. Nakashima, M. Murakawa and N. Mataga, Bull. Chem. Soc. Jpn., 1976, 49, 854.
67. W. Rettig and M. Zander, Ber. Bunsen-Ges. Phys. Chem., 1983, 87, 1143.
68. M. Zander and W. Rettig, Chem. Phys. Lett., 1984, 110, 602.
69. W. Rettig, Appl. Phys. B, 1988, 45, 145.
70. E. Lippert, W. Rettig, V. Bonacic-Koutecky, F. Heisel and J. A. Miehé, Adv. Chem. Phys., 1987, 68, 1.
71. W. Rettig, in Modern Models of Bonding and Delocalization, ed. J. Liebman and A. Greenberg, VCH Publishers, New York, 1988, ch. 5, p. 229.
72. M. Schütz and R. Schmidt., J. Phys. Chem., 1996, 100, 2112.
73. K. Elich, M. Kitazawa, T. Okada and R. Wortmann, J. Phys. Chem. A, 1997, 101, 2010.
74. N. Mataga, H. Yao, T. Okada and W. Rettig, J. Phys. Chem., 1989, 93, 3383.
75. H. Lueck, M. W. Windsor and W. Rettig, J. Phys. Chem., 1990, 94, 4550.
76. In earlier works, this state is often called LE state (locally excited) although the excitation is not localized in the symmetric cases studied here.
77. T. Hayashi, T. Suzuki, N. Mataga, Y. Sakata and S. Misumi, J. Phys. Chem., 1977, 81, 420.
78. H. Yao, T. Okado and N. Mataga, J. Phys. Chem., 1989, 93, 7388.
79. J.-P. Desvergne, N. Bitit and H. Bouas-Laurent, J. Chem. Res. 1984, (S) 214; (M) 1901.
80. J.-P. Desvergne, N. Bitit and H. Bouas-Laurent, J. Chem. Res. 1984, (S) 214; (M) 1901.
81. M. Vogel and W. Rettig, Ber. Bunsen-Ges. Phys. Chem., 1987, 91, 1241.
82. (a) H. Herbst, Ph.D. Thesis, University of Mainz, 1990;
83. (b) D. Bender, H. Herbst, P. Schade and K. Müllen, Chem. Ber., 1988, 121, 1177;
84. (c) J. Mortensen, J. Heinze, H. Herbst and K. Müllen, J. Electroanal. Chem., 1992, 324, 201;
85. (d) F. Krollpfeiffer and J. Branscheid, Ber. Dtsch. Chem. Ges., 1923, 56, 1617.
86. A. Sieglitz and R. Marx, Ber. Dtsch. Chem. Gesell., 1923, 56, 1619.
87. J. Fiedler, W. Huber and K. Müllen, Angew. Chem., Int. Ed. Engl., 1986, 25, 443.
88. D. Bender, H. Unterberg and K. Müllen, Angew. Chem., Int. Ed. Engl., 1986, 25, 444.
89. A. J. Beckwith and W. A. Waters, J. Chem. Soc., 1956, 1108.
90. F. H. C. Stewart, Aust. J. Chem., 1961, 14, 177; 1968, 21, 1107.
91. F. H. C. Stewart, Aust. J. Chem., 1961, 14, 177; 1968, 21, 1107.
92. G. Felix, R. Lapouyade, A. Castellan and H. Bouas-Laurent, Tetrahedron Lett., 1975, 409.
93. D. E. Applequist and D. J. Swart, J. Org. Chem., 1975, 40, 1800.
94. F. Bell and D. H. Waring, J. Chem. Soc., 1949, 267.
95. (a) J. H. Golden, J. Chem. Soc., 1961, 3741;
96. (b) J. Ferguson, Chem. Rev., 1986, 86, 957;
97. (c) J. Harada, K. Ogawa and S. Tomoda, Chem. Lett., 1995, 751;
98. (d) T. R. Battersby, P. Gantzel, K. K. Baldridge and J. S. Siegel, Tetrahedron Lett., 1995, 36, 845.
99. H. D. Becker, S. R. Hall, B. W. Skelton and A. H. White, Aust. J. Chem., 1982, 35, 2357.
100. T. Förster, Pure Appl. Chem., 1962, 4, 121.
101. G. Swiatkowski, R. Menzel and W. Rapp, J. Lumin., 1987, 37, 183.
102. C. Cornelißen, W. Rettig, J.-P. Desvergne and H. Bouas-Laurent, Chem. Phys. Lett., 1995, 239, 290; C. Cornelißen-Gude and W. Rettig, Chem. Phys., 1998, 229, 325.
103. C. Cornelißen, W. Rettig, J.-P. Desvergne and H. Bouas-Laurent, Chem. Phys. Lett., 1995, 239, 290; C. Cornelißen-Gude and W. Rettig, Chem. Phys., 1998, 229, 325.
104. K. Yamasaki, K. Arita and O. Kajimoto, Chem. Phys. Lett., 1986, 123, 277.
105. L. R. Khundkar and A. H. Zewail, J. Chem. Phys., 1986, 84, 1302.