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■ 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 K_a = 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.