Face selectivity of inclusion complexation of viologens with β-cyclodextrin and 6-O-(2-sulfonato-6-naphthyl)-β-cyclodextrin

Journal of Physical Chemistry B

Volumn 106, Issue 29, 2002, Pages 7186-7192

  Park, Joon Woo ^a   Song, Hee Eun ^a   Lee, Soo Yeon ^a  

^a Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

VIOLOGENS;

BIOMIMETIC MATERIALS; ELECTRON TRANSITIONS; FLUORESCENCE; HYDROPHOBICITY; QUENCHING; SOLUTIONS;

COMPLEXATION;

EID: 0037173869     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp020428f     Document Type: Article

References (58)

1. For compilations on recent researches on cyclodextrins, see: (a) Comprehensive Supramolecular Chemistry; Szejtli, J., Osa, T., Eds.; Pergamon Press: Oxford 1996; Vol. 3.
2. (b) Chem. Rev. 1998, 98, 1741-2076.
3. Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803.
4. (a) Schneider, H.-J.; Hacket, F.; Rüdiger, V. Chem. Rev. 1998, 98, 1755 and references therein.
5. (b) Bergeron, R.J.; Channing, M.A.; Gilbeily, G.J.; Pillor, D.M. J. Am. Chem. Soc. 1977, 99, 5146.
6. (c) Bergeron, R.J.; Channing, M.A.; McGovern, K.A.; Roberts, W.P. Bioorg. Chem. 1979, 8, 263.
7. (d) Yoshida, N.; Seiyama, A.; Fujimoto, M. J. Phys. Chem. 1990, 94, 4254.
8. (e) Kano, K.; Karo, Y.; Kodera, M. J. Chem. Soc., Perkin Trans. 2 1996, 1211.
9. (f) Fronza, G.; Mele, A.; Redenti, E.; Ventura, P. J. Org. Chem. 1996, 61, 909.
10. (g) Kano, K.; Kamo, H.; Negi, S.; Kitae, T.; Takaoka, R.; Yamaguchi, M.; Okubo, H.; Hirama, M. J. Chem. Soc., Perkin Trans. 2 1999, 15.
11. (h) Heda, S.; Ishikawa, S.; Neya, S.; Funasaki, N. J. Phys. Chem. B 1999, 103, 2579.
12. (i) Ishizu, T.; Kintsu, K.; Yamamoto, H. J. Phys. Chem. B 1999, 103, 8992.
13. Gelb, R.I.; Schwartz, L.M.; Laufer, D.A. J. Chem. Soc., Perkin Trans. 2 1984, 15.
14. (a) Rüdiger, V.; Eliseev, A.; Simova, S.; Schneider, H.-J.; Blandamer, M.J.; Cullis, P.M.; Meyer, A.J. J. Chem. Soc., Perkin Trans. 2 1996, 2119.
15. (b) McAlpine, S.R.; Garcia-Garibay, M.A. J. Org. Chem. 1996, 61, 8307.
16. (a) Kodaka, M.; Fukaya, T. Bull. Chem. Soc. Jpn. 1986, 59, 2032.
17. (b) Kodaka, M.; Fukaya, T. Bull, Chem. Soc. Jpn. 1989, 62, 1154.
18. Kodaka, M. J. Am. Chem. Soc. 1993, 115, 3702.
19. (a) Kodaka, M.; Fukaya, T. Bull. Chem. Soc. Jpn. 1975, 48, 375.
20. (b) Shimizu, H.; Katto, A.; Hatano, M. Bull. Chem. Soc. Jpn. 1979, 52, 2678.
21. (c) Krois, D.; Brinker, U.H. J. Am. Chem. Soc. 1998, 120, 11627.
22. (d) Kodaka, M. J. Phys. Chem. A 1998, 102, 8101.
23. (e) Zhang, X.; Nau, W.M. Angew. Chem., Int. Ed. 2000, 39, 544.
24. (g) Bobek, M.M.; Krois, D.; Brinker, U.H. Org. Lett. 2000, 2, 1999.
25. (h) Mayer, B.; Zhang, X.Y.; Nan, W.M.; Marconi, G. J. Am. Chem. Soc. 2001, 123, 5240.
26. Lipkowitz, K.B. Chem. Rev. 1998, 98, 1829 and references therein.
27. Liu, L.; Guo, Q.-X. J. Phys. Chem. B 1999, 103, 3461.
28. Rekharsky, M.V.; Inoue, Y. Chem. Rev. 1998, 98, 1875 and references therein.
29. Park, J.W.; Song, H.J. J. Phys. Chem. 1989, 93, 6454.
30. Park, J.W.; Park, K.H. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 277.
31. Park, J.W.; Choi, N.H.; Kim, J.H. J. Phys. Chem. 1996, 100, 769.
32. (a) Quintela, P.A.; Diaz, A.; Kaifer, A.E. Langmuir 1988, 4, 663.
33. (b) Diaz, A.; Quintela, P.A.; Schuette, J.M.; Kaifer, A.E. J. Phys. Chem. 1988, 92, 3537.
34. (c) Lee, C.; Kim, C.; Park, J.W. J. Electroanal. Chem. 1994, 374, 115.
35. (d) Mirzoian, A.; Kaifer, A.E. Chem. Eur. J. 1997, 3, 1052.
36. (e) John, S.A.; Okajima, T.; Ohsaka, T. J. Electroanal. Chem. 1999, 466, 67.
37. (f) Mu, T.W.; Lin, L.; Li, X.S.; Guo, Q.X. J. Phys. Org. Chem. 2001, 14, 559.
38. (a) Sakurai, M.; Kitagawa, M.; Hoshi, H.; Inoue, Y.; Chujo, R. Chem. Lett. 1988, 895.
39. (b) Kitagawa, M.; Hoshi, H.; Sakurai, M.; Inoue, Y.; Chujo, R. Bull. Chem. Soc. Jpn. 1988, 16, 4225.
40. Park, J.W.; Song, H.E.; Lee, S.Y. J. Phys. Chem. B 2002, 106, 5177.
41. Kodaka, M. J. Phys. Chem. A 1998, 102, 8101.
42. Ikeda, H.; Du, Y.; Nakamura, A.; Toda, F. Chem. Lett. 1991, 1198.
43. (a) Yoon, K.B. Chem. Rev. 1993, 93, 321.
44. (b) Le, T.P.; Rogers, J.E.; Kelly, L.A. J. Phys. Chem. A 2000, 104, 6778.
45. Park, J.W.; Park, S.H.; Lee, B.A.; Lee, S.Y. Chem. Lett. 1997, 1043.
46. Park, J.W.; Lee, B.A.; Lee, S.Y. J. Phys. Chem. 1998, 102, 8209.
47. (a) Kuroda, Y.; Ito, M.; Sera, T.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 7003.
48. (b) Acquavella, M.F.; Evans, M.E.; Farraher, S.W.; Nevoret, C.J.; Abelt, C.J. J. Chem. Soc., Perkin Trans. 2 1995, 385.
49. (c) Hubbard, B.K.; Beilstein, L.A.; Heath, C.E.; Abelt, C.J. J. Chem. Soc., Perkin Trans. 2 1996, 10.
50. To avoid the complications from the dynamic quenching, the data taken at [Viologen] ≤ 1.0 mM were used for fitting.
51. Yonemoto, E.H.; Saupe, G.B.; Schmehl, R.H.; Hubig, S.M.; Riley, R.L.; Iverson, B.L.; Mallouk, T.E. J. Am. Chem. Soc. 1994, 116, 4786.
52. +.
53. (a) Hwang, H.J.; Lee, S.K.; Lee, S.; Park, J.W. J. Chem. Soc., Perkin Trans. 2 1999, 1081.
54. (b) Hwang, H.J.; Lee, S.; Park, J.W. Bull. Korean Chem. Soc. 2000, 21, 245.
55. (a) Davies, D.M.; Savage, J.R. J. Chem. Res. (S) 1993, 94; J. Chem. Res. (M), 1993, 660.
56. (a) Davies, D.M.; Savage, J.R. J. Chem. Res. (S) 1993, 94; J. Chem. Res. (M), 1993, 660.
57. (b) Davies, D.M.; Deary, M.E. J. Chem. Soc., Perkin Trans. 2 1995, 1287.
58. (c) Davies, D.M.; Deary, M.E.; Wealleans, D.I. J. Chem. Soc., Perkin Trans. 2 1998, 193.