A modified cyclodextrin with a fully encapsulated dansyl group: Self-inclusion in the solid state and in solution

Chemistry - A European Journal

Volumn 2, Issue 4, 1996, Pages 373-381

  Corradini, Roberto ^a   Dossena, Arnaldo ^a   Marchelli, Rosangela ^a   Panagia, Anna ^a   Sartor, Giorgio ^a   Saviano, Michele ^b   Lombardi, Angela ^b   Pavone, Vincenzo ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Crystal structure; Cyclodextrins; Dansyl derivatives; Fluorescence sensors; Self inclusion

Indexed keywords

CIRCULAR DICHROISM SPECTRA; CYCLODEXTRIN CAVITIES; FLUORESCENCE INTENSITIES; FLUORESCENCE SENSORS; FLUORESCENCE SPECTRA; MODIFIED CYCLODEXTRINS; SELF-INCLUSION; TIME-RESOLVED FLUORESCENCE;

CRYSTAL STRUCTURE; FLUORESCENCE; FLUOROPHORES; HYDROGEN BONDS; MESOPOROUS MATERIALS; NAPHTHALENE; SENSORS; SULFUR COMPOUNDS;

CYCLODEXTRINS;

EID: 0000877962     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020404     Document Type: Article

References (72)

1. W. Saenger, Angew. Chem. Int. Ed. Engl. 1980, 19, 344-362.
2. W. Saenger in Inclusion compounds, Vol. 2 (Eds.: J. E. D. Davies, D. D. McNicol, J. L. Atwood), Academic Press, London, 1984, pp. 231-255.
3. G. Wenz, Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822.
4. a) K. Harata, J. Chem. Soc. Chem. Commun. 1993, 546-547;
5. b) K. Harata, H. Uedaira, Bull. Chem. Soc. Jpn. 1975, 48, 375-378;
6. c) G. S. Cox, N. J. Turro, N. C. Yang, M. J. Chen, J. Am. Chem. Soc. 1984, 106, 422-424.
7. a) M. R. Eftink, M. L. Andy, K. Bystrom, H. D. Perlmutter, D. S. Kristol, J. Am. Chem. Soc. 1989, 111, 6765-6772;
8. b) M. Komyiama, M. L. Bender, ibid. 1978, 100, 2259-2260.
9. a) I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856;
10. b) I. Tabushi, Y. Kiyosuke, T. Sugimoto, K. Yamamura, ibid. 1978, 100, 916-919.
11. a) I. Tabushi, Y. Kuroda, T. Mizutani, J. Am. Chem. Soc. 1986, 108, 4514-4518;
12. b) A. V. Eliseev, H.-J. Schneider, Angew. Chem. Int. Ed. Engl. 1993, 32, 1331-1333.
13. R. P. Frankewich, K. N. Thimmaiah, W. L. Hinze, Anal. Chem. 1991, 63, 2924-2933.
14. D. F. Eaton, Tetrahedron 1987, 43, 1551-1570.
15. a) S. Li, W. C. Purdy, Chem. Rev. 1992, 92, 1457-1470;
16. b) T. Kinoshita, F. Iinuma, A. Tsuji, Chem. Pharm. Bull. 1974, 22, 2413-2420.
17. Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. Int. Ed. Engl. 1992, 31, 745-747.
18. a) A. Ueno, Adv. Mater. 1993, 5, 132-134
19. b) A. Ueno, T. Kuwabara, A. Nakamura, F. Toda, Nature 1992, 356, 136-137.
20. A. Ueno, Q. Chen, I. Suzuki, T. Osa, Anal. Chem. 1992, 64, 1650-1655.
21. a) A. Ueno, F. Moriwaki, T. Osa, F. Hamada, K. Murai, J. Am. Chem. Soc. 1988, 110, 4323-4328;
22. b) A. Ueno, F. Moriwaki, A. Azuma, T. Osa, J. Org. Chem. 1989, 54, 295-299.
23. a) A. Ueno, I. Suzuki, T. Osa, J. Am. Chem. Soc. 1989, 111, 6391-6397;
24. b) I. Suzuki, A. Ueno, T. Osa, Chem. Lett. 1989, 2013-2016;
25. c) A. Ueno, I. Suzuki, T. Osa, Chem. Lett. 1989, 1059-1062.
26. a) A. Ueno, Y. Tomita, T. Osa, J. Chem. Soc. Chem. Commun. 1983, 976-977;
27. b) A. Ueno, F. Moriwaki, T. Osa, F. Hamada, K. Murai, Tetrahedron 1987, 43, 1571-1578.
28. Y. Wang, T. Ikeda, A. Ueno, F. Toda, Tetrahedron Lett. 1993, 34, 4971-4974.
29. a) K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I. Suzuki, T. Osa, J. Am. Chem. Soc. 1993, 115, 5035-5040.
30. b) K. Hamasaki, A. Ueno, F. Toda, I. Suzuki, T. Osa, Bull. Chem. Soc. Jpn. 1994, 67, 516-523.
31. A. Ueno, S. Minato, I. Suzuki, M. Fukushima, M. Ohkubo, T. Osa, F. Hamada, K. Murai, Chem. Lett. 1990, 605-608.
32. Y. Wang, T. Ikeda, H. Ikeda, A. Ueno, F. Toda, Bull. Chem. Soc. Jpn. 1994, 67, 1598-1607.
33. R. A. Dunbar, F. V. Bright, Supramol. Chem. 1994, 3, 93-99.
34. U. Narang, R. A. Dunbar, F. V. Bright, P. N. Prasad, Appl. Spectrosc. 1993, 47, 1700-1703.
35. a) W. L. Hinze, T. E. Riehl, D. W. Armstrong, W. DeMond, A. Alak, T. Ward, Anal. Chem. 1985, 57, 237-242;
36. b) K. Fujimura, S. Suzuki, K. Hayashi, S. Masuda, ibid. 1990, 62, 2198-2205;
37. c) S. H. Lee, A. Berthod, D. W. Armstrong, J. Chromatogr. 1992, 603, 83-93;
38. d) T. Takeuchi, H. Asai, D. Ishii, ibid. 1986, 357, 409-415.
39. a) D. W. Armstrong, F. Y. He, S. M. Han, J. Chromatogr. 1988, 448, 345-354;
40. b) W. L. Hinze, D. Y. Pharr, Z. S. Fu, W. G. Burkert, Anal. Chem. 1989, 61, 422-428.
41. a) S. Terabe, Y. Miyashita, Y. Ishihama, O. Shibata, J. Chromatogr. 1993, 636, 47-55.
42. b) A. Guttman, A. Paulus, A. S. Cohen, N. Grinberg, B. L. Karger, ibid. 1988, 448, 41-53.
43. H. L. Jin, A. Stalcup, D. W. Armstrong, Chirality 1989, 1, 137-141.
44. R. Corradini, G. Sartor, R. Marchelli, A. Dossena, A. Spisni, J. Chem. Soc. Perkin Trans. 2 1992, 1979-1983.
45. G. Impellizzeri, G. Maccarrone, E. Rizzarelli, G. Vecchio, R. Corradini, R. Marchelli, Angew. Chem. Int. Ed. Engl. 1991, 30, 1348-1349.
46. R. Corradini, G. Impellizzeri, G. Maccarrone, R. Marchelli, E. Rizzarelli, G. Vecchio, in Chemistry and Properties of Biomolecular Systems (Eds.: E. Rizzarelli, T. Theophanides) Kluwer, Dordrecht, 1991, pp. 209-221.
47. R. P. Bonomo, V. Cucinotta, F. D'Alessandro, G. Impellizzeri, G. Maccarrone, G. Vecchio, E. Rizzarelli, Inorg. Chem. 1991, 30, 2708-2713.
48. K. Hirotsu, T. Higuchi, K. Fujita, T. Ueda, A. Shinoda, T. Imoto, I. Tabushi, J. Org. Chem. 1982, 47, 1143-1144.
49. S. Kamitori, K. Hirotsu, T. Higuchi, K. Fujita, H. Yamamura, T. Imoto, I. Tabushi, J. Chem. Soc. Perkin Trans. 2 1987, 7-14.
50. B. Di Blasio, V. Pavone, F. Nastri, C. Isernia, M. Saviano, C. Pedone, V. Cucinotta, G. Impellizzeri, E. Rizzarelli, G. Vecchio, Proc. Natl. Acad. Sci. USA 1992, 89, 7218-7221.
51. K. Harata in Inclusion Compounds, Vol.5 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Oxford University Press, Oxford, UK, 1991, Chapt. 9, pp. 311-344.
52. K. Harata, K. Uekama, M. Otagiri, F. Hirayama, Y. Ohtani, Bull Chem. Soc. Jpn. 1985, 58, 1234-1238.
53. a) A. A. Bothner-By, R. L. Stephens, J. Lee, C. D. Warren, R. W. Jeanloz, J. Am. Chem. Soc. 1984, 106, 811-813;
54. b) A. Bax, D. G. Davis, J. Magn. Res. 1985, 63, 207-213.
55. a) W. Saka, Y. Yamamoto, Y. Inoue, R. Chujo, K. Takahashi, K. Hattori, Bull. Chem. Soc. Jpn. 1990, 63, 3175-3182;
56. b) H. Ikeda, H.-T. Moon, Y.-Q. Du, F. Toda, Supramol. Chem. 1993, 1, 337-342.
57. Y. H. Li, L. M. Chan, L. Tyer, R. T. Moody, C. M. Himel, D. M. Hercules, J. Am. Chem. Soc. 1975, 97, 3118-3126.
58. M. Kodaka, J. Phys. Chem. 1991, 95, 2110-2112.
59. H. Shimizu, A. Kaito, M. Hatano, Bull. Chem. Soc. Jpn. 1979, 52, 2678-2684.
60. K. Kano, Y. Tamiya, C. Otsuki, T. Shimomura, T. Ohno, O. Hayashida, Y. Murakami, Supramol. Chem. 1993, 2, 137-143.
61. D. V. O'Connor, D. Phillips, Time Correlated Single Photon Counting, Associated Press, London, 1984.
62. a) C. D. Tran, J. H. Fendler, J. Phys. Chem. 1984, 88, 2167-2173;
63. b) G. Nelson, G. Patonay, I. M. Warner, Appl. Spectrosc. 1987, 41, 1235-1238;
64. c) F. V. Bright, G. C. Catena, J. Huang, J. Am. Chem. Soc. 1990, 112, 1343-1346.
65. W. Y. Lin, H. E. Van Wart, J. Inorg. Biochem. 1988, 32, 21-38.
66. G. Battistuzzi Gavioli, G. Grandi, L. Menabue, G. C. Pellacani, M. Sola, J. Chem. Soc. Dalton Trans. 1985, 2363-2368.
67. L. Antolini, L. Menabue, M. Sola, L. P. Battaglia, A. Bonamartini Corradi, J. Chem. Soc. Dalton Trans. 1986, 1367-1373.
68. A. Altomare, G. Cascarano, C. Gacovazzo, A. Guagliardi, G. Polidori, M. C. Burla, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
69. Enraf Nonius, Molen Package (1988), Enraf Nonius, Delft, The Netherlands.
70. D. T. Cromer, J. T. Waber, International Tables for X-Ray Crystallography, Vol. 4, Kynoch Press, Birmingham, England, 1984, Table 2.2 B, p. 99.
71. J. R. Knutson, J. M. Beechem, L. Brand, Chem. Phys. Lett. 1983, 102, 501-507.
72. R. Corradini, A. Dossena, G. Impellizzeri, G. Maccarrone, R. Marchelli, E. Rizzarelli, G. Sartor, G. Vecchio, J. Am. Chem. Soc. 1994, 116, 10267-10273.