pH- and H2O-driven triple-mode pyrene fluorescence

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3841-3844

  Shiraishi, Yasuhiro ^a   Tokitoh, Yasufumi ^a   Hirai, Takayuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748600682     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0614673     Document Type: Article

References (39)

1. (a) Balzani, V. Molecular Devices and Machines: A Journey into the Nano World; Wiley-VCH: Weinheim, 2003.
2. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
3. (c) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
4. (d) Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecular Recognition; American Chemical Society: Washington, DC, 1992.
5. (a) Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: London, 1970.
6. (b) Winnik, F. M. Chem. Rev. 1993, 93, 587-614.
7. For example: (a) Redpath, A. E. C.; Winnik, M. A. J. Am. Chem. Soc. 1982, 104, 5604-5607.
8. (b) Kim, S. K.; Lee, S. H.; Lee, J. Y.; Bartsch, R. A.; Kim, J. S. J. Am. Chem. Soc. 2004, 126, 16499-16506.
9. (c) Yang, R.-H.; Chan, W.-H.; Lee, A. W. M.; Xia, P.-F.; Zhang, H.-K.; Li, K.'A. J. Am. Chem. Soc. 2003, 125, 2884-2885.
10. (d) Suzuki, Y.; Morozumi, T.; Nakamura, H.; Shimomura, M.; Hayashita, T.; Bartsh, R. A. J. Phys. Chem. B 1998, 102, 7910-7917.
11. (e) Bodenant, B.; Fages, F.; Delville, M.-H. J. Am. Chem. Soc. 1998, 120, 7511-7519.
12. (f) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464.
13. (a) Winnik, M. A.; Bystryak, S. M.; Liu, Z.; Siddiqui, J. Macromolecules 1998, 31, 6855-6864.
14. (b) Seixas de Melo, J.; Costa, T.; Miguel, M. da G.; Lindman, B.; Schillén, K. J. Phys. Chem. B 2003, 107, 12605-12621.
15. (c) Winnik, F. M. Macromolecules 1987, 20, 2745-2750.
16. (d) Cho, H. K.; Lee, D. H.; Hong, J.-I. Chem. Commun. 2005, 1690-1692.
17. (e) Fujimoto, K.; Muto, Y.; Inouye, M. Chem. Commun. 2005, 4780-4782.
18. (a) Yang, J.-S.; Lin, C.-S.; Hwang, C.-Y. Org. Lett. 2001, 3, 889-892.
19. (b) Kim, S. K.; Bok, J. H.; Bartsch, R. A.; Lee, J. Y.; Kim, J. S. Org. Lett. 2005, 7, 4839-4842.
20. (c) Martínez, R.; Espinosa, A.; Tárraga, A.; Molina, P. Org. Lett. 2005, 7, 5869-5872.
21. 10
22. Sancenón, F.; Descalzo, A. B.; Lloris, J. M.; Martínez- Máñez, R.; Pardo, T.; Seguí, M. J.; Soto, J. Polyhedron 2002, 21, 1397-1404.
23. 10
24. 10
25. See Supporting Information.
26. (a) Shiraishi, Y.; Tokitoh, Y.; Nishimura, G.; Hirai, T. Org. Lett. 2005, 7, 2611-2614.
27. (b) Nishimura, G.; Shiraishi, Y.; Hirai, T. Chem. Commun. 2005, 5313-5315.
28. (c) Shiraishi, Y.; Tokitoh, Y.; Hirai, T. Chem. Commun. 2005, 5316-5318.
29. (d) Albelda, M. T.; Bernardo, M. A.; Díaz, P.; García-España, E.; Seixas de Melo, J.; Pina, F.; Soriano, C.; Luis, S. V. Chem. Commun. 2001, 1520-1521.
30. 10). In addition, filtration of the L1 solution does not lead to a decrease in the intensities of excimer emission and the absorption band. These findings exclude the possibility of an intermolecular aggregation of L1 in solution.
31. (a) Ueno, A.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1989, 111, 6391-6397.
32. (b) Strauss, J.; Daub, J. Org. Lett. 2002, 4, 683-686.
33. Martinho, J. M. G.; Castanheira, E. M. S.; Reis e Sousa, A. T.; Saghbini, S.; Andre, J. C.; Winnik, M. A. Macromolecules 1995, 28, 1167-1171.
34. 1d
35. Pant, D.; Levinger, N. E. J. Phys. Chem. B 1999, 103, 7846-7852.
36. 2O solvation becomes weaker with a rise in temperature: Szabo, M. I. A.; Goring, D. A. I. J. Chem. Soc. A 1968, 1500-1503.
37. Ghosh, A. S.; Basu, S. J. Photochem. 1974, 3, 247-248.
38. (b) Ghosh, A. S.; Basu, S. Indian J. Chem. 1975, 13, 952.
39. (c) Castanheira, E. M. S.; Martinho, J. M. G. Chem. Phys. Lett. 1991, 185, 319-323.