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Communication | Special issue | Vol 74, No. 1, 2007, pp.251-257
Published online, 20th November, 2007
DOI: 10.3987/COM-07-S(W)80
Synthesis and Properties of Bis(1,3-benzodithiole)-Type Redox Systems Containing a Xylyl Rotator Unit: A New Type of Redox-Responsive Molecular Rotor

Yuzuru Uchiyama, Akira Ohta,* and Kunihide Fujimori

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

Abstract

A new type of redox-responsive molecular rotors (32+/4) possessing a xylyl rotator unit have been designed and synthesized. Reduction of 32+ with zinc gave the corresponding cyclization products (4), from which dications (32+) were regenerated upon oxidation. Cyclic voltammetry also showed the interconversion between 32+ and 4. Variable-temperature 1H NMR measurements revealed that the rotational barriers of the xylyl units in the neutral states (4) are higher than those in the dication states (32+).