Supramolecular probe for bicarbonate exhibiting anomalous pyrene fluorescence in aqueous media

Journal of the American Chemical Society

Volumn 128, Issue 14, 2006, Pages 4498-4499

  Suzuki, Iwao ^a   Ui, Mihoko ^a   Yamauchi, Akiyo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICARBONATE; CYCLODEXTRIN; PYRENE; TRANSITION ELEMENT; ZINC;

AQUEOUS SOLUTION; ARTICLE; CIRCULAR DICHROISM; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PH; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; ULTRAVIOLET RADIATION;

BICARBONATES; CIRCULAR DICHROISM; GAMMA-CYCLODEXTRINS; HYDROGEN-ION CONCENTRATION; KINETICS; MOLECULAR CONFORMATION; PYRENES; SPECTROMETRY, FLUORESCENCE; WATER;

EID: 33646066573     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055772f     Document Type: Article

References (26)

1. (a) de Silva, A. P.; Gunaratne, H. Q. N.; Huxley, A. J.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
2. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
3. (c) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155-3184.
4. (d) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2534-2574.
5. (e) Beer, P. D.; Gale, P. D. Angew. Chem., Int. Ed. 2001, 40, 486-516.
6. (a) Yamauchi, A.; Hayashita, T.; Nishizawa, S.; Watanabe, M.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 2319-2320.
7. (b) Kwon, J. K.; Singh, N. J.; Kim, H. N.; Kim, S. K.; Kim, K. S.; Yoon, J. J. Am. Chem. Soc. 2004, 126, 8892-8893.
8. (c) Aoki, S.; Kagata, D.; Shiro, M.; Takeda, K.; Kimura, E. J. Am. Chem. Soc. 2004, 126, 13377-13390.
9. (d) Zhang, J.; Davidson, M. G.; Mahon, M. F.; Kociok-Köhn, G.; James, T. D. J. Am. Chem. Soc. 2004, 126, 16179-16186.
10. (a) Kimura, E. Acc. Chem. Res. 2001, 34, 171-179.
11. (b) Linares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57-75.
12. (c) Schmuck, C.; Schwegmann, M. J. Am. Chem. Soc. 2005, 127, 3373-3379.
13. (a) Beer, P. D.; Cadman, J.; Lloris, J. M.; Martínez- Máòez, R.; Padilla, M. E.; Pardo, T.; Smith, D. K.; Soto, J. J. Chem. Soc., Dalton Trans. 1999, 127-133.
14. (b) Mizutani, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. J. Am. Chem. Soc. 2002, 124, 3920-3925.
15. (c) Badugu, R.; Lakowicz, J. R.; Geddes, C. D. J. Am. Chem. Soc. 2005, 127, 3635-3641.
16. (a) Zhang, X.; von Eldic, R.; Koike, T.; Kimura, E. Inorg. Chem. 1993, 32, 5749-5755.
17. (b) Bruce, J. I.; Dickins, R. S.; Govenlock, L. J.; Gunnlaugsson, T.; Lopinski, S.; Lowe, M. P.; Peacock, R. D.; Perry, J. J. B.; Aime, S.; Botta, M. J. Am. Chem. Soc. 2000, 122, 9674-9684.
18. (c) Hennrich, G.; Sonnenshein, H.; Resch-Genger, U. Tetrahedron Lett. 2001, 42, 2805-2808.
19. (d) Bretonnliere, Y.; Cann, M. J.; Slater, R. Org. Bioorg. Chem. 2004, 2, 1624-1632.
20. (a) Chen, Y.; Cann, M. J.; Litvin, T. N.; Iourgenko, V.; Sinclair, M. L.; Levin, L. R.; Buck, J. Science 2000, 289, 625-628.
21. (b) Zippin, J. H.; Levin, L. R.; Buck, J. Trends Endocrinol. Metab. 2001, 12, 366-370.
22. Ueno, A.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1989, 111, 6391-6397.
23. +.
24. See Supporting Information for complete details of the association dimer formation of 1.
25. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; Tokyo-Kagaku-Dojin: Tokyo, 1982.
26. Wahl, P.; Krieger, C.; Schweitzer, D.; Staab, H. A. Chem. Ber. 1984, 117, 260-276.