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■ Synthesis and Photoswitchable Complexation/Extraction Properties of Lipophilic Azabis(benzo-15-crown-5) Ionophores for Alkali Metal Cations

Kazunori Odashima,* Koji Tohda, Shinji Yoshiyagawa, Shinichiro Yamashita, Masamitsu Kataoka, and Yoshio Umezawa*

*Graduate School of Pharmaceutical Science, University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033

Abstract

Novel lipophilic derivatives of azobis(benzo-15-crown-5) (1b, 1c) were synthesized and their photoisomerization, complexation and extraction properties for alkali metal cations were investigated. Upon UV light irradiation, the photostationary state of the trans and cis isomers was reached and, with both 1b and 1c, the extractabilities of Rb⁺ and Cs⁺ increased due to the formation of 1:1 sandwich-type complexes by the cis isomers. On the other hand, the extractability of K⁺ decreased, possibly because the 2:1 complexes formed by the trans isomers are more stable and/or lipophilic than the complexes of the cis isomers.