Complexation between Rhodamine B (RB) and sulfonated calix [n] arenes (SCnA) were studied by means of UV-vis spectroscopy and fluorescence spectroscopy. In the presence of sulfonated calix[n] arenes, the absorption band of Rhodamine B shifts to longer wavelength and its intensity decreases. The formation of a host-guest type complex also results in the fluorescence quenching of Rhodamine B. The association constants for the RB/SCnA complexes increase in the order of SC4A < SC6A < SC8A and show dependence on the size of the cavities of the calixarenes. The fluorescence is selectively regenerated by adding acetylcholine. Based on this observation, a method to determine acetylcholine in a real neutral aqueous medium was developed.

References

1 Bohmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
10.1002/anie.199507131
CAS Web of Science® Google Scholar
2 Shinkai, S. Tetrahedron 1993, 49, 8933.
10.1016/S0040-4020(01)91215-3
CAS Web of Science® Google Scholar
3 McKervey, A.; Bohmer, V. Chem. Brit. 1992, 724.
Google Scholar
4 Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053.
10.1021/ja00181a004
CAS Web of Science® Google Scholar
5 Shinkai, S.; Araki, K.; Matsuda, T.; Manabe, O. Bull. Chem. Soc. Jpn. 1989, 62, 3856.
10.1246/bcsj.62.3856
CAS Web of Science® Google Scholar
6 Shinkai, S.; Araki, K.; Manabe, O. J. Am. Chem. Soc. 1988, 110, 7214.
10.1021/ja00229a046
CAS Web of Science® Google Scholar
7 Arena, G.; Casnati, A.; Contino, A.; Gulino, F. G.; Sciotto, D.; Ungaro, R. J. Chem. Soc., Parian Trans. 2, 2000, 419.
Google Scholar
8 Liu, Y.; Han, B. H.; Chen, Y. T. J. Org. Chem. 2000, 65, 6227.
10.1021/jo991654x
CAS PubMed Web of Science® Google Scholar
9 Nishida, M.; Ishii, D.; Yoshida, I.; Shinka, S. Bull. Chem. Soc. Jpn. 1997, 70, 2131.
10.1246/bcsj.70.2131
CAS Web of Science® Google Scholar
10 Tao, W.; Barra, M. J. Chem. Soc., Perkin Trans. 2 1998, 1957.
Google Scholar
11 Inouye, M.; Hashimoto, K.; Isagawa, K. J. Am. Chem. Soc. 1994, 116, 5517.
10.1021/ja00091a085
CAS Web of Science® Google Scholar
12 Koh, K. N.; Araki, K.; Ikeda, A.; Otsuka, H.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 755.
10.1021/ja951488k
CAS Web of Science® Google Scholar
13(a) Gutsche, C. D.; Iqbal, M. Org. Synth. 1990, 68, 234.
10.15227/orgsyn.068.0234
CAS Web of Science® Google Scholar
(b) Gutsche, C. D.; Dhawan, B.; Leonis, M.; Stewart, D. Org. Synth. 1990, 68, 238.
10.15227/orgsyn.068.0238
CAS Web of Science® Google Scholar
(c) Munch, J. H.; Gutsche, C. D. Org. Synth. 1990, 68, 243.
10.15227/orgsyn.068.0243
CAS Web of Science® Google Scholar
14 Shinkai, S.; Kawaguchi, H.; Manabe, O. J. Polym. Sci. C: Polym. Lett. 1988, 26, 391.
10.1002/pol.1988.140260903
CAS Web of Science® Google Scholar
15 Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
10.1021/ja01176a030
CAS Web of Science® Google Scholar

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Volume20, Issue4

April 2002

Pages 322-326

Interaction of Sulfonated Calix[n]arenes with Rhodamine B and Its Application to Determine Acetylcholine in a Real Neutral Aqueous Medium

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Interaction of Sulfonated Calix[n]arenes with Rhodamine B and Its Application to Determine Acetylcholine in a Real Neutral Aqueous Medium

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