New fluorescent "off-on" behavior of 9-anthryl aromatic amides through controlling the twisted intramolecular charge transfer relaxation process by complexation with metal ions

Journal of Physical Chemistry B

Volumn 105, Issue 15, 2001, Pages 2923-2931

  Morozumi, Tatsuya ^a   Anada, Takahisa ^a   Nakamura, Hiroshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRYL AROMATIC AMIDES; CARBONYL GROUP; ETHYLENOXY MOIETY; FLUOROPHORES; TWISTED INTRAMOLECULAR CHARGE TRANSFER RELAXATION PROCESS;

BARIUM; CALCIUM; CHARGE TRANSFER; CHEMICAL RELAXATION; COMPLEXATION; FLUORESCENCE; MAGNESIUM PRINTING PLATES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHERS; POSITIVE IONS; STRONTIUM; ULTRAVIOLET SPECTROSCOPY;

AROMATIC POLYMERS;

EID: 0037134605     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0030600     Document Type: Article

References (76)

1. Lehn, J.-M. Siipramolecular Chemistry; VCH: Weinheim, Germany, 1995.
2. de Suva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxely, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice T. E. Chem. Rev. 1997, 97, 1515 and references therein.
3. Balzani, V.; Scandola, F. Siipramolecular Photochemistry; EllisHonvood: Chichester, U.K., 1991.
4. Scneider, H.-J.; Durr, H. Frontiers in Supramoleciilear Organic Chemistry and Photochemistry; VCH: Weinheim, Germany, 1991.
5. Czarnik, A. W. Fluorescent Cliemosensors for Ion and Molecule Recognition; American Chemical Society: Washington, DC, 1992.
6. Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry: London, 1991.
7. Hiraoka, M. Crown Ethers and Analogous Compounds; Elesevier: New York, 1992.
8. Takagi, M.; Ueno, K. Host Guest Complex Chemistry; Springer: Berlin, 1984.
9. Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry; SpringerVerlag: New York, 1978.
10. D'Souza, V. T.; Lipokwitz, K. B. Chem. Rev. 1998, 98, 1741.
11. Shinkai, S. Tetrahedron 1993, 49, 8933.
12. Shinkai, S. Advances in Supramolecular Chemistry; JAI Press: Greenwich, CT, 1993; Vol. 3.
13. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: London, 1989.
14. Takagi, M.; Nakamura, H.; Ueno, K. Anal. Lett. 1977, 10, 1115.
15. Dix, J. P.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1978, 17, 857.
16. Takagi, M.; Nakamura, H. J. Coord. Chem. 1986, 15, 53.
17. Hayashita, T.; Teramae, N.; Kuboyama, T.; Nakamura, S.; Yamamoto, H.; Nakamura, H. J. Inclusion Plienom. 1998,32,251 and references therein.
18. Sousa, L. R.; Larson, J. M. J. Am. Chem. Soc. 1977, 99, 307.
19. Larson, J. M.; Sousa, L. R. J. Am. Chem. Soc. 1978, 100, 1943.
20. Vögtle, F.; Weber, E. Angew. Chem., Int. Ed. Engl. 1979, 18, 753.
21. Tummler, B.; Maass, G.; Weber, E.; Wehner, W.; Vögtle, F. J. Am. Chem. Soc. 1977, 99, 4683.
22. Down, J. L.; Lewis, J.; Moore, B.; Wilkinsons, G. W. Proc. Chem. Soc. 1957, 209.
23. Down, J. L.; Lewis, J.; Moore, B.; Wilkinsons, G. W. J. Chem. Soc. 1959, 3767.
24. Ray, A.; Nemthy, G. J. Am. Chem. Soc. 1971, 93, 6787.
25. Schott, H.; Kyuhan, S. J. Phann. Sci. 1975, 64, 663.
26. Lundberg, R. D.; Bailey, F. E.; Callard, R. W. J. Polym. Sci., Part A-I 1966, 4, 1563.
27. Yamazaki, N.; Nakahama, S.; Hirao, A.; Negi, S. Tetrahedron Lett. 1978, 2494.
28. Kubokawa, H.; Yamaguchi, K.; Hirao, A.; Nakahama, S.; Yamazaki, N. Chem. Lett. 1982, 1937.
29. Yamazaki, N.; Hirao, A.; Nakahama, S. J. Macromol. Sci., Chem. 1979, A13, 321.
30. Kuboniwa, H.; Nagami, S.; Yamaguchi, K.; Hirao, A.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Chem. Commun. 1985, 1468.
31. Kuboniwa, H.; Yamaguchi, K.; Hirao, A.; Nakahama, S.; Hori, K.; Ohashi, Y. Chem. Lett. 1988, 923.
32. Kasuga, N.; Nakahama, S.; Yamasuchi, K.; Ohashi, Y.; Hori, K. Bull. Chem. Soc. Jpn. 1991, 64, 3584.
33. Gardner, J. O.; Beard, C. C. J. Med. Chem. 1978, 21, 357.
34. Hiratani, K.; Aiba, S.; Nakagawa, T. Chem. Lett. 1980, 477.
35. Hiratani, K. Chem. Lett. 1981, 21.
36. Hiratani, K.; Sugihara, H.; Kasuga, K.; Fujiwara, K.; Hayashita, T.; Bartsch, R. A. J. Chem. Soc., Chem. Commun. 1994, 319.
37. Choy, E. M.; Evans, D. F.; Cussler, E. L. J. Am. Chem. Soc. 1974, 96, 7085.
38. Duax, W. L.; Smith, G. D.; Strong, P. D. J. Am. Chem. Soc. 1980, 102, 6725.
39. Kakizawa, A.; Akita, T.; Nakamura, H. Chem. Lett. 1993, 1671.
40. Tahara, R.; Hasebe, K.; Nakamura, H. Chem. Lett. 1995, 753.
41. Suzuki, Y.; Morozumi, T.; Kakizawa, Y.; Bartsch, R. A.; Hayashita, T.; Nakamura, H. Chem. Lett. 1996, 617.
42. Tahara, R.; Morozumi, T.; Suzuki, Y.; Kakizawa, Y.; Akita, T.; Nakamura, H. J. Inclusion Phenom. 1998, 32, 283.
43. Suzuki, Y.; Morozumi, T.; Nakamura, H.; Shimomura, M.; Hayashita, T.; Bartsch, R. A. J. Phys. Chem. B 1998, 102, 7910.
44. Anada, T.; Kitaoka, T.; Ota, H.; Kakizawa, Y.; Akita, Y.; Morozumi, T.; Nakamura, H. Bunseki Kagaku 1999, 48, 1107.
45. Bezilevskaya, N. S.; Cherkasov, A. S. Opt. Spectrosc. 1965, 18, 30.
46. Bezilevskaya, N. S.; Cherkasov, A. S. Zli.'Prikl. Spectrosk. Akad. Nauk Belorussk. SSR 1965, 3, 548.
47. Werner, T. C.; Hercules, D. M. J. Phys. Chem. 1969, 73, 2005.
48. Suzuki, S.; Fuji, T.; Yoshiike, N.; Komatsu, S.; Iida, T. Bull. Chem. Soc. Jpn. 1978, 51, 2460.
49. Agbaria, R. A.; Butterfield, M. T.; Wamar, I. M. J. Phys. Chem. 1996, 100, 17133.
50. Werner, T. C.; Rodgers, J. J. Photochem. 1986, 32, 59.
51. Chae, M. Y.; Czarnik, A. W. J. Fhioresc. 1992, 2, 225.
52. De Santis, G.; Fabrizzi, L.; Licchelli, M.; Mangano, C.; Sacchi, D. Inorg. Chem. 1995, 34, 3581.
53. Rotkiewicz, K.; Grellmann, K. H.; Grabowski, Z. R. Chem. Phys. Lett. 1973, 19, 315.
54. Grabowski, Z. R.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J.; Baumann, W. Nouv. J. Chim. 1979, 3, 443.
55. Rettig, W. Top Curr. Chem. 1994, 169, 253.
56. Schneider, F.; Lippert, E. Ber. Bunsen-Ges. Phys. Chem. 1968, 72, 1155.
57. Schneider, F.; Lippert, E. Ber. Bunsen-Ges. Phys. Chem. 1970, 74, 624.
58. Okada, T.; Malaga, N.; Baumann, W.; Siemiarczuk, A. J. Phys. Chem. 1987, 91, 4490.
59. Wiessner, A.; Huttmann, G.; Kuhnle, W.; Staeek, H. J. Phys. Chem. 1995, 99, 14923.
60. Dey, J.; Dogra, S. K. J. Chem. Phys. 1994, 98, 3638.
61. Dey, J.; Warner, I. M. J. Phys. Chem. A 1997, 101, 4872.
62. Azumaya, I.; Kagechika, H.; Fujiwara, Y.; Itoh, M.; Yamaguchi, K.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 2833.
63. Lewis, F. D.; Long, T. M. J. Phys. Chem. A 1998, 102, 5327.
64. Braun, D.; Retlig, W.; Delmond, S.; Letard, J.-F.; Lapouyade, R. J. Phys. Chem. A 1997, 101, 6836.
65. de Suva, A. P.; de Suva, S. A. J. Chem. Soc., Chem. Commun. 1987, 1709.
66. Bissell, R. A.; Calle, E.; de Suva, A. P.; de Suva, S. A.; Gunaratne, H. Q. N.; Habib-Jiwan, J.-L.; Peiris, A. S. L.; Rupasighe, R. A. D. D.; Samarasinghe, T. K. S.; Sandanayake, K. R. A. S.; Soumillion, J.-P. J. Chem. Soc., Perkin Trans. 2 1992, 1559.
67. de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Nature 1993, 364, 42.
68. de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. J. Am. Chem. Soc. 1997, 119, 7891.
69. Czamik, A. W. Ace. Chem. Res. 1994, 27, 302.
70. Huston, M. E.; Haider, K. W.; Czarnik, A. W. J. Am. Chem. Soc. 1988, 110, 4460.
71. Huston, M. E.; Engleman, C.; Czamik, A. W. J. Am. Chem. Soc. 1990, 112, 7054.
72. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Sacchi, D.; Taalietti, A. Analyst 1996, 121, 1763.
73. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Perotti, A.; Taglietti, A.; Sacchi, D. Chem. Eur. J. 1996, 2, 75.
74. Santis, G. D.; Fabbrizzi, L.; Licchelli, M.; Poggi, A.; Taglietti, A. Angen: Chem., Int. Ed. Engl. 1996, 35, 202.
75. O'Connell, E. J., Jr.; Delmauro, M.; Irwin, J. Photochem. Photobiol 1971, 14, 189.
76. Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 77, 431.