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Paper | Special issue | Vol 67, No. 2, 2006, pp.665-678
Published online, 16th September, 2005
DOI: 10.3987/COM-05-S(T)55
Novel 9,10-Bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene Derivatives Bridged by a Crown Ether Unit at the 1,8-Positions: A New Type of Redox-switchable Hosts Undergoing Reversible Structural Changes

Akira Ohta,* Taeko Numae, Yoshiro Yamashita, and Kunihide Fujimori*

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto 390-8621, Japan

Abstract

Novel redox-switchable host molecules (2) composed of a 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene unit and a crown ether moiety bridging the 1,8-positions have been synthesized. Cyclic voltammetry and X-Ray analyses revealed that the molecules undergo a significant structural change upon oxidation. 1H-NMR titration experiments on the neutral and dication states show that the binding abilities of the dication states for alkali metal cations (Li+, Na+, K+) are considerably lower than those of the neutral molecules. The binding properties of 2 were also investigated by cyclic voltammetry.