Molecular recognition by a silica-bound fullerene derivative

Journal of the American Chemical Society

Volumn 119, Issue 32, 1997, Pages 7550-7554

  Bianco, Alberto ^a   Gasparrini, Francesco ^b   Maggini, Michele ^a   Misiti, Domenico ^b   Polese, Alessandra ^a   Prato, Maurizio ^c   Scorrano, Gianfranco ^a   Toniolo, Claudio ^a   Villani, Claudio ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATERIALS; MOLECULAR RECOGNITION; PROTEIN ANALYSIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030812150     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970502l     Document Type: Article

References (53)

1. (a) Gügel, A.; Beker, M.; Hammel, D.; Mindach, L.; Rader, J.; Simon, T.; Wagner, M.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 644-646.
2. (b) Welch, C. J.; Pirkle, W. H. J. Chromatogr. 1992, 609, 89-101.
3. (c) Jinno, K.; Ohta, H.; Saito, Y.; Uemura, T. J. Chromatogr. 1993, 648, 71-77.
4. (d) Kibbey, C. E.; Savina, M. R.; Parseghian, B. K.; Francis, A. H. Anal. Chem. 1993, 65, 3717-3719.
5. (e) Kimata, K.; Hosoya, K.; Araki, T.; Tanaka, N. J. Org. Chem. 1993, 58, 282-283.
6. (f) Herren, D.; Thilgen, C.; Calzaferri, G.; Diederich, F. J. Chromatogr. 1993, 644, 188-192.
7. (g) Saito, Y.; Ohta, H.; Nagashima, H.; Itoh, K. J. Liq. Chromatogr. 1994, 17, 2359-2372.
8. (h) Xiao, J.; Meyerhoff, M. E. J. Chromatogr. A 1995, 715, 19-29.
9. (a) Nagashima, H.; Terasaki, H; Saito, K.; Jinno, K.; Itoh, K. J. Org. Chem. 1995, 60, 4966-4967.
10. (b) Saito, Y.; Ohta, H.; Terasaki, H.; Katoh, Y.; Nagashima, H.; Jinno, K.; Itoh, K.; Trengove, R. D.; Harrowfield, J.; Li, S. F. J. J. High Resolut. Chromatogr. 1996, 19, 475-477.
11. (c) Chang, C.-S.; Wen, C.-H.; Den, T.-G. Huaxue 1996, 54, 11-21; Chem. Abstr. 1997, 126, 139272d.
12. (c) Chang, C.-S.; Wen, C.-H.; Den, T.-G. Huaxue 1996, 54, 11-21; Chem. Abstr. 1997, 126, 139272d.
13. (a) Sijbesma, R.; Srdanov, G.; Wudl, F.; Castoro, J. A.; Wilkins, C.; Friedman, S. H.; DeCamp, D. L.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6510-6512.
14. (b) Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palù, G.; Blair, E. D. J. Med. Chem. 1994, 37, 4558-4562.
15. (c) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem. 1996, 4, 767-779.
16. (d) Da Ros, T.; Prato, M.; Novello, F.; Maggini, M.; Banfi, E. J. Org. Chem. 1996, 61, 9070-9072.
17. Mirkin, C. A.; Caldwell, W. B. Tetrahedron 1996, 52, 5113-5130.
18. (a) Chupa, J. A.; Xu, S.; Fischetti, R. F.; Strongin, R. M.; McCauley, J. P.; Smith, A. B.; Blasie, J. K.; Peticolas, L. J.; Bean, J. C. J. Am. Chem. Soc. 1993, 115, 4383-4384.
19. (b) Chen, K.; Caldwell, W. B.; Mirkin, C. A. J. Am. Chem. Soc. 1993, 115, 1193-1194.
20. (c) Geckeler, K. E.; Hirsch, A. J. Am. Chem. Soc. 1993, 115, 3850-3851.
21. (d) Bergbreiter, D. E.; Gray, H. N. J. Chem. Soc., Chem. Commun. 1993, 645-646.
22. (e) Liu, B.; Bunker, C. E.; Sun, Y. J. Chem. Soc., Chem. Commun. 1996, 1241-1242.
23. (f) Planeix, J.; Coq, B.; de Menorva, L.; Medina, P. J. Chem. Soc., Chem. Commun. 1996, 2087-2088.
24. (g) Stalling, D. L; Guo, C.; Kuo, K. C.; Saim. S. J. Microcolumn Sep. 1996, 5, 223-235.
25. (h) Stalling, D. L; Guo, C.; Saim. S. J. Chromatogr. Sci. 1993, 31, 265-278.
26. (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798-9799.
27. (b) Bianco, A.; Maggini, M.; Scorrano, G.; Toniolo, C.; Marconi, G.; Villani, C.; Prato, M. J. Am. Chem. Soc. 1996, 118, 4072-4080.
28. (c) Prato, M.; Maggini, M.; Giacometti, C.; Scorrano, G.; Sandonà, G.; Farnia, G. Tetrahedron 1996, 52, 5221-5234.
29. (a) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229-231.
30. (b) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699-702.
31. (c) Williams, R. M.; Zwier, J. M.; Verhoeven, J. W.; Nachtegaal, G. H.; Kentgens, A. P. M. J. Am. Chem. Soc. 1994, 116, 6965-6966.
32. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Tetrahedron Lett. 1995, 249-252.
33. (e) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2269-2271.
34. (f) Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. J. Chem. Soc., Chem. Commun. 1996, 2615-2616. See also: Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260. Averdung, J.; Gerkensmeier, T.; Ito, O.; Luftmann, H.; Luger, P.; Schlachter, I.; Siedschlag, C.; Torres-García, G.; Mattay, J. In Fullerenes and Fullerene Nanostructures; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1996; pp 509-514. Averdung, J.; Budwach, T.; Iwanek, W.; Schlachter, I.; Torres-García, G.; Mattay, J. In Physics and Chemistry of Fullerenes and Derivatives; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1995; pp 137-141.
35. (f) Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. J. Chem. Soc., Chem. Commun. 1996, 2615-2616. See also: Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260. Averdung, J.; Gerkensmeier, T.; Ito, O.; Luftmann, H.; Luger, P.; Schlachter, I.; Siedschlag, C.; Torres-García, G.; Mattay, J. In Fullerenes and Fullerene Nanostructures; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1996; pp 509-514. Averdung, J.; Budwach, T.; Iwanek, W.; Schlachter, I.; Torres-García, G.; Mattay, J. In Physics and Chemistry of Fullerenes and Derivatives; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1995; pp 137-141.
36. (f) Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. J. Chem. Soc., Chem. Commun. 1996, 2615-2616. See also: Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260. Averdung, J.; Gerkensmeier, T.; Ito, O.; Luftmann, H.; Luger, P.; Schlachter, I.; Siedschlag, C.; Torres-García, G.; Mattay, J. In Fullerenes and Fullerene Nanostructures; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1996; pp 509-514. Averdung, J.; Budwach, T.; Iwanek, W.; Schlachter, I.; Torres-García, G.; Mattay, J. In Physics and Chemistry of Fullerenes and Derivatives; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1995; pp 137-141.
37. (f) Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. J. Chem. Soc., Chem. Commun. 1996, 2615-2616. See also: Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 259-260. Averdung, J.; Gerkensmeier, T.; Ito, O.; Luftmann, H.; Luger, P.; Schlachter, I.; Siedschlag, C.; Torres-García, G.; Mattay, J. In Fullerenes and Fullerene Nanostructures; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1996; pp 509-514. Averdung, J.; Budwach, T.; Iwanek, W.; Schlachter, I.; Torres-García, G.; Mattay, J. In Physics and Chemistry of Fullerenes and Derivatives; Kuzmany, H., Fink, J., Mehring, M., Roth, S., Eds.; World Scientific: Singapore, 1995; pp 137-141.
38. 2 (50/50) as eluent) the capacity factors for the calix-[8]-, -[6]-, and -[4]arenes are 0.07, 0.27, and 0.47, respectively; i.e., the elution order is inverted compared to 3 for calix[4]-and calix[8]arenes.
39. Gutsche, C. D., Gutsche, E.; Karaulov, I. J. Inclusion Phenom. 1985, 3, 447-451.
40. Polar, H-bond-forming solvents like acetone and pyridine are known to alter the conformational behavior of calixarenes: Gutsche, C. D.; Bauer, L. J. J. Am. Chem. Soc. 1985, 107, 6052-6059.
41. (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström, O. J. Chem. Soc., Chem. Commun. 1992, 604-606.
42. (b) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597-1599.
43. (c) Andersson, T.; Westman, G.; Wennerström, O. Sundahl, M. J. Chem. Soc., Perkin Trans. 2 1994, 1097-1101.
44. (d) Priyadarsini, K. I.; Mohan, H.; Tyagi, A. K.; Mittal, J. P. J. Phys. Chem. 1994, 98, 4756-4759.
45. (a) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756.
46. (b) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009.
47. (c) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353.
48. Bianco, A.; Crisma, M.; Valle, G; Formaggio, F. Toniolo, C. Unpublished results.
49. Balch, A. L.; Catalano, V. J.; Lee, J. W.; Olmestead, M. M. J. Am. Chem. Soc. 1992, 114, 5455-5457.
50. (a) Crane, J. D.; Hitchcock, P. B.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1992, 1764-1765.
51. (b) Birkett, P. R.; Crane, J. D.; Hitchcock, P. B.; Kroto, H. W.; Meidine, M. F.; Taylor, R.; Walton, R. M. J. Mol. Struct. 1993, 292, 1.
52. Novello, F.; Prato, M.; Da Ros, T.; De Amici, M.; Bianco, A.; Toniolo C.; Maggini, M. Chem. Commun. 1996, 903-904.
53. Baldwin, J. E.; Spivey, A. C.; Schofield, C. J.; Sweeney, J. B.; Tetrahedron 1993, 49, 6309-6330.