Interaction of 4-hydroxybiphenyl with cyclodextrins: Effect of complex structure on spectroscopic and photophysical properties

Chemistry - A European Journal

Volumn 6, Issue 9, 2000, Pages 1578-1591

  Bortolus, Pietro ^a   Marconi, Giancarlo ^a   Monti, Sandra ^a   Mayer, Bernd ^b   Köhler, Gottfried ^b   Grabner, Gottfried ^b  

^a Istituto di Fotochimica e Radiazioni d'Alta Energia   (Italy)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

Circular dichroism; Cyclodextrins; Photophysics; Structure elucidation

Indexed keywords

4 HYDROXYBIPHENYL; 4-PHENYLPHENOL; BIPHENYL DERIVATIVE; CYCLODEXTRIN; DEXTRIN; HYDROXYL GROUP;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; COMPLEX FORMATION; MOLECULAR INTERACTION; PHOTOCHEMISTRY; QUANTUM THEORY; REACTION ANALYSIS; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYSTEM ANALYSIS; TEMPERATURE;

EID: 0034595264     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000502)6:9<1578::AID-CHEM1578>3.3.CO;2-S     Document Type: Article

References (64)

1. M. L. Bender, M. Komiyama, Cyclodextrin Chemistry, Springer, Berlin, 1978.
2. J. Szejtli, Cyclodextrins and Their Inclusion Complexes, Akademiai Kiado, Budapest. 1982.
3. V. Balzani, L. De Cola, Supramolecular Chemistry, Kluwer, Dordrecht, 1992.
4. P. Bortolus, S. Monti, Adv. Photochem. 1996, 21, 1-133.
5. a) N. Kobayashi, R. Saito, Y. Hino, A. Ueno, T. Osa. J. Chem. Soc. Chem. Commun. 1982, 706-707
6. b) T. Tamaki, Chem. Lett. 1984, 53-56
7. c) T. Tamaki, T. Kokubu, J. Incl. Phenom. 1984, 2, 815-822
8. d) M. Ohashi, K. Kasatani, H. Shinohara, H. Sato, J. Am. Chem. Soc. 1990, 112, 5824-5830.
9. a) N. Kobayashi, R. Saito, H. Hino, Y. Hino. A. Ueno, T. Osa, J. Chem. Soc. Perkin Trans. II 1983, 1031-1035
10. b) S. Hamai, J. Phys. Chem. 1989, 93, 6527-6529
11. c) V. Pushkara Rao, N.J. Turro, Tetrahedron Lett. 1989, 30, 4641-4644
12. d) V. Buss, Angew. Chem. 1991, 103, 889-890; Angew. Chem. Int. Ed. Engl. 1991, 30, 869-870
13. d) V. Buss, Angew. Chem. 1991, 103, 889-890; Angew. Chem. Int. Ed. Engl. 1991, 30, 869-870
14. d) A. Nakamura, S. Sato, K. Hamasaki, A. Ueno, F. Toda, J. Phys. Chem. 1995, 99, 10952-10959.
15. X. Shen, M. Belletête, G. Durocher, J. Phys. Chem. B 1998, 102, 1877-1883.
16. a) A. Harada, J. Li, M. Kamachi, Nature 1992, 356, 325-327
17. b) A. Harada, J. Li, M. Kamachi, Nature 1994, 370, 126-128
18. B. Mayer, C. T. Klein, I. N. Topchieva, G. Köhler, J. Comput. Aided Mol. Des. 1999, 13, 373-383.
19. V. Ramamurthy, Tetrahedron 1986, 42, 5753-5839.
20. a) N. Chattopadhyay, T. Chakraborty, A. Nag, M. Chowdhury, J. Photochem. Photobiol. A: Chem. 1990, 52, 199-204
21. b) N. Chattopadhyay, J. Photochem. Photobiol. A: Chem. 1991, 58, 31-36
22. c) N. Chattopadhyay, R. Dutta, M. Chowdhury, Indian J. Chem. 1992, 31 A, 512-517.
23. J. E. Hansen, E. Pines, G. R. Fleming, J. Phys. Chem. 1992, 96, 6904-6910.
24. a) T. Yorozu, M. Hoshino, M. Imamura, H. Shizuka, J. Phys. Chem. 1982, 86, 4422-4426
25. b) D. F. Eaton. Tetrahedron 1987, 43, 1551-1570
26. H.-R. Park, B. Mayer, P. Wolschann, G. Köhler, J. Phys. Chem. 1994, 98, 6158-6166.
27. S. Monti, G. Köhler, G. Grahner. J. Phys. Chem. 1993, 97, 13011-13016.
28. R. Townsend, S. G. Schulman, Chimica Oggi 1992, 10, 49-52.
29. H. H. Jaffé, M. Orchin in Theory and Applications of Ultraviolet Spectra. Wiley, New York, 1962, pp. 397-407.
30. L. S. Rosenberg, G. Lam, G. Groh, S. G. Schulman, Anal. Chim. Acta 1979, 106, 81-87.
31. A. Muñoz de la Peña, A. Fernánden Gutiérrez, S. G. Schulman, Anal. Lett. 1985, 18, 2489-2495.
32. a) H. Suzuki, Bull. Chem. Soc. Jpn. 1959, 32, 1340-1350
33. b) T. Fujii, S. Suzuki, S. Komatsu, Chem. Phys. Lett. 1978, 57, 175-178
34. c) T. Fujii, S. Komatsu, S. Suzuki, Bull. Chem. Soc. Jpn. 1982, 55, 2516-2520
35. d) H.-S. Im, E. R. Bernstein, J. Chem. Phys. 1988, 88, 7337-7345.
36. a) J. M. Bello, R. J. Hurtubise, Anal. Chem. 1987, 59, 2395-2400
37. h) J. M. Bello, R. J. Hurtubise, Appl. Spectrosc. 1988, 42, 619-623.
38. G. Grabner, N. Getoff, T. Gantchev, D. Angelov, M. Shopova, Photochem. Photobiol. 1991, 54, 673-681.
39. N. L. Allinger, Y. H. Yuh, J. H. Lee, J. Am. Chem. Soc. 1989, 111, 8551-8566.
40. C. Betzel, W. Saenger, B. E. Hingerty, G. M. Brown, J. Am. Chem. Soc. 1984, 106, 7545-7557.
41. a) N. Metropolis, A. W. Rosenbluth, M. B. Rosenbluth, A. H. Teller, J. Chem. Phys. 1953, 21, 1087-1092
42. b) S. Kirkpatrick, C. D. Gelatt, M. P. Vecchi, Science 1983, 220, 671-680.
43. Program Package MultiMize, B. Mayer, Vienna, Austria 1997.
44. B. Mayer, G. Marconi, C. T. Klein, G. Köhler, J. Ind. Phenom. Molec. Recogn. Chem. 1997, 29, 79-93.
45. G. Grabner, S. Monti, G. Marconi, B. Mayer, C. T. Klein. G. Köhler, J. Phys. Chem. 1996, 100, 20068-20075.
46. G. Marconi, B. Mayer, C. T. Klein, G. Köhler, Chem. Phys. Lett. 1996, 260, 589-594.
47. I. Tinoco, Jr., Adv. Chem. Phys. 1962, 4, 113-160.
48. J. A. Schellman, Acc. Chem. Res. 1968, 1, 144-151.
49. M. T. Beck, in Chemistry of Complex Equilibria, Van Nostrand, New York, 1970, ch. 5.
50. K. A. Connors, Chem. Rev. 1997, 97, 1325-1357, and references therein.
51. M. Kamiya, S. Mitsuhashi, M. Makino, H. Yoshioka, J. Chem. Phys. 1992, 96, 95-99.
52. D. W. Cho, Y. K. Kim, S. G. Kang, M. Yoon, J. Phys. Chem. 1994, 98, 558-562.
53. S.-F. Lin, K. A. Connors, J. Pharm. Sci. 1983, 72, 1333-1338.
54. G. L. Bertrand, J. R. Faulkner, Jr., S. M. Han, D. W. Armstrong, J. Phys. Chem. 1989, 93, 6863-6867.
55. M. V. Rekharsky, Y. Inoue, Chem. Rev. 1998, 98, 1875-1917.
56. W. C. Cromwell, K. Bystrom, M. R. Eftink, J. Phys. Chem. 1985, 89, 326-332.
57. M. R. Eftink, M. L. Andy, K. Bystrom, H. D. Perlmutter, D. S. Kristol, J. Am. Chem. Soc. 1989, 111, 6765-6772.
58. I. Carmichael, G. L Hug., J. Phys. Chem. Ref. Data 1986, 15, 1-250.
59. D. Eisenherg, W. Kauzmann, The Structure and Properties of Water, Clarendon Press, Oxford, 1969, p. 205.
60. B. Amand, R. Bensasson, Chem. Phys. Lett. 1975, 34, 44-48.
61. a) G. L. Hug, I. Carmichael, J. Photochem. 1985, 31, 179-192
62. b) I. Carmichael, G. L. Hug, J. Phys. Chem. 1985, 89, 4036-4039.
63. E. C. Lim, and Y. H. Li, J. Chem. Phys. 1970, 52, 6416-6422.
64. K. Razi Naqvi, J. Donatch, U. P. Wild, Chem. Phys. Lett. 1975, 34, 285-288, and references therein.