A novel antenna cyclodextrin: Synthesis and photosensitized reaction of an included guest

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4364-4368

  Nowakowska, Maria ^a,b   Loukine, Nikolai ^a   Gravett, David M ^a   Burke, Nicholas A D ^a   Guillet, James E ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PHOTOSENSITIZATION; SOLUBILITY; SYNTHESIS;

EID: 0031007383     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963072s     Document Type: Article

References (46)

1. Holden, D. A.; Rendall, W. A.; Guillet, J. E. Ann. N.Y. Acad. Sci. 1981, 366, 11.
2. Guillet, J. E.; Rendall, W. A. Macromolecules 1986, 19, 224.
3. Guillet, J. E.; Wang, J.; Gu, L. Macromolecules 1986, 19, 2793.
4. Nowakowska, M.; White, B.; Guillet, J. E. Macromolecules 1989, 22, 3903.
5. Nowakowska, M.; White, B.; Guillet, J. E. Macromolecules 1988, 21, 3430.
6. Nowakowska, M.; White, B.; Guillet, J. E. Macromolecules 1989, 22, 2317.
7. Nowakowska, M.; Sustar, E.; Guillet, J. E. J. Am. Chem. Soc. 1991, 113, 253.
8. Nowakowska, M.; Foyle, V. P.; Guillet, J. E. J. Am. Chem. Soc. 1993, 115, 5975.
9. Guillet, J. E.; Burke, N. A. D.; Nowakowska, M.; Reese, H.; Gravett, D. M. Macromol. Symp. 1995, 98, 53.
10. Gravett, D. M.; Guillet, J. E. Macromolecules 1996, 29, 617.
11. Gravett, D. M.; Guillet, J. E. J. Am. Chem. Soc. 1993, 115, 5970.
12. Szejtli, J. Cyclodextrins and Their Inclusion Complexes; Akademiai Kiado: Budapest, 1971.
13. Ramamurthy, V.; Eaton, D. F. Acc. Chem. Res. 1988, 21, 300. Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Toronto, 1991; p 295.
14. Ramamurthy, V.; Eaton, D. F. Acc. Chem. Res. 1988, 21, 300. Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Toronto, 1991; p 295.
15. Tabushi, I.; Fujita, K.; Yuan, L. C. Tetrahedron Lett. 1977, 2503.
16. Gonzalez, M. C.; McIntosh, A. R.; Bolton, J. R.; Weedon, A. C. J. Chem. Soc., Chem. Commun. 1984, 1138.
17. Neckers, D. C.; Paczkowski, J. J. Am. Chem. Soc. 1986, 108, 291. Neckers, D. C.; Paczkowski, J. Tetrahedron 1986, 42, 4671.
18. Neckers, D. C.; Paczkowski, J. J. Am. Chem. Soc. 1986, 108, 291. Neckers, D. C.; Paczkowski, J. Tetrahedron 1986, 42, 4671.
19. Aquino, A. M.; Abelt, C. J.; Berger, K. L.; Darragh, C. M.; Kelley, S. E.; Cossette, M. V. J. Am. Chem. Soc. 1990, 112, 5819.
20. During review of this manuscript, a paper (Wang, P. F.; Jullien, L.; Valeur, B.; Filhol, J.-S.; Canceill, J.; Lehn, J.-M. New J. Chem. 1996, 20, 895) appeared describing the isomerization of a nitrone sensitized by an antenna cyclodextrin. We thank a referee for bringing this publication to our attention.
21. Jullien, L.; Canceill, J.; Valeur, B.; Bardez, E.; Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2438. Jullien, L.; Canceill, J.; Valeur, B.; Bardez, E.; Lefevre, J.-P.; Lehn, J.-M.; Marchi-Artzner, V.; Pansu, R. J. Am. Chem. Soc. 1996, 118, 5432.
22. Jullien, L.; Canceill, J.; Valeur, B.; Bardez, E.; Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2438. Jullien, L.; Canceill, J.; Valeur, B.; Bardez, E.; Lefevre, J.-P.; Lehn, J.-M.; Marchi-Artzner, V.; Pansu, R. J. Am. Chem. Soc. 1996, 118, 5432.
23. Blyshak, L. A.; Dodson, K. Y.; Patonay, G.; Warner, I. M.; May, W. E. Anal. Chem. 1989, 61, 955.
24. Holden, D. A.; Guillet, J. E. Macromolecules 1980, 13, 289.
25. Brimacombe, J. S.; Jones, B. D.; Stacey, M.; Willard, J. J. Carbohydr. Res. 1966, 2, 167.
26. Przybylski, M.; Glocker, M. O. Angew. Chem., Int. Ed. Engl 1996, 35, 807.
27. Huang, E. C.; Henion, J. D. Rapid Commun. Mass Spectrom. 1990, 4, 467.
28. Tinke, A. P.; van der Hoeven, R. A. M.; Niessen, M. W. A.; van der Greef, J.; Vincken, J.-P.; Schols, H. A. J. Chromatogr. 1993, 647, 279.
29. Bates, P. S.; Parker, D.; Patti, A. F. J. Chem. Soc., Perkin Trans. 2 1994, 657.
30. Bates, P. S.; Parker, D.; Green, B. N. J. Chem. Soc., Chem. Commun. 1993, 693.
31. Camillieri, P.; Haskins, N. J.; New, A. P.; Saunders, M. R. Rapid Commun. Mass Spectrom. 1993, 7, 949.
32. Bates, P. S.; Kataky, R.; Parker, D. Analyst 1994, 119, 181.
33. Camillieri, P.; Haskins, N. J.; Howlett, D. R. FEBS Lett. 1994, 341, 256.
34. Haskins, N. J.; Saunders, M. R.; Camillieri, P. Rapid Commun. Mass Spectrom. 1994, 8, 423.
35. Ramanathan, R.; Prokai, L. J. Am. Soc. Mass Spectrom. 1995, 6, 866.
36. Kelly, P. M.; Kataky, R.; Parker, D.; Patti, A. F. J. Chem. Soc., Perkin Trans. 2 1995, 1955.
37. Cunniff, J. B.; Vouros, P. J. Am. Soc. Mass Spectrom. 1995, 6, 437.
38. Lippmann, T.; Wilde, H.; Pink, M.; Schäfer, A.; Hesse, M.; Mann, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1195.
39. Ganem, B.; Li, Y.-T.; Henion, J. D. J. Am. Chem. Soc. 1991, 113, 6294.
40. Ganem, B.; Li, Y.-T.; Henion, J. D. J. Am. Chem Soc. 1991, 113, 7818.
41. Smith, R. D.; Light-Wahl, K. J. Biol. Mass Spectrom. 1993, 22, 493.
42. Li, Y.-T.; Hsieh, Y. L., Henion, J. D.; Ocain, T. D.; Schiehser, G. A.; Ganem, B. J. Am. Chem. Soc. 1994, 116, 7487.
43. Howard, J. A.; Tait, J. C. J. Org. Chem. 1978, 43, 4279.
44. Modi, P. J.; Guillet, J. E.; Scaiano, J. C.; Wintgens, V. J. Photochem. Photobiol. A 1994, 81, 87.
45. Stein, S. E.; Golden, D. M. J. Org. Chem. 1977, 42, 839.
46. Herndon, W. C. J. Org. Chem. 1981, 46, 2119.