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Paper | Regular issue | Vol 60, No. 1, 2003, pp.143-150
Published online, 25th November, 2002
DOI: 10.3987/COM-02-9646
A Pseudo Thiacrown Compound Formed by Hydrophobic Interaction of Its Lipophilic Parts in Water: Ag+-Selective Fluorophore in Water

Seiichi Inokuma, Susumu Nishio, Takashi Funaki, Norio Atarashi, Tetsuya Shirakawa, and Jun Nishimura*

*Department of Chemistry, Faculty of Engineering, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan

Abstract

Amphiphilic podand (3) was prepared by conventional thioether synthesis in ethanol. It shows exclusive selectivity toward Ag+ ion in a liquid-liquid extraction. It was also found to exhibit selective fluorescence decrease only in the presence of Ag+ ion in water. From the fluorometric titration, the complexing stability constant toward Ag+ in water estimated to be log Ka = 4.2, which value is comparable to cyclic dithia-18-crown-6. This extraordinarily high value was caused by a pseudo cyclic structure formed in water, which was supported by 1H NMR spectral analysis.