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2018, Vol.47, No.4

536-539

The Switching from Cis-to-trans One-way Photoisomerization to Mutual Photoisomerization of a Stilbene–Urea Compound Triggered by Proton Transfer Reaction

Hisato Matsumoto ,Haruki Masai ,Yoshinobu Nishimura , and Tatsuo Arai *
Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba, Ibaraki 305-8571, Japan
https://doi.org/10.1246/cl.171222

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Abstract

We have developed a new photochromic material containing a stilbene moiety and a urea moiety based on cooperative effect of photoisomerization and proton transfer. An anthracene–urea–stilbene compound (stAn) exhibited cis-to-trans one-way photoisomerization via the excited triplet state. Furthermore, we succeeded in the switching from one-way to mutual photoisomerizations by the addition of a fluoride ion, which causes the ground state intermolecular proton transfer of stAn leading to negligible intersystem crossing from the excited singlet state.

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We have developed a new photochromic material containing a stilbene moiety and a urea moiety based on the molecular design involved in photoisomerization and proton transfer. An anthracene–urea–stilbene compounds exhibited cis-to-trans one-way photoisomerization. In addition, we succeeded in the control between mutual and cis-to-trans one-way photoisomerization by the addition of TBAF.

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