Diarylethenes that Photoswitch with Visible Light

Chapter

Abstract

Two approaches to prepare visible-light-sensitive diarylethene (DAE) derivatives are described. One is direct excitation of well-designed DAE derivatives with visible light and the other is indirect visible-light excitation to a reactive triplet state by a triplet energy transfer. The absorption spectra of both open- and closed-ring isomers of DAE are dependent not only on the aryl groups, but also on the ethene bridge. Introduction of dicyanoethene, maleic anhydride, or maleimide to the ethene bridge shifts the absorption bands of the open-ring isomers to the visible wavelength region. DAEs having an aromatic dye in the central reactive carbon atom were designed and their photochromic as well as fluorescence performance upon irradiation with visible light was studied. DAE-perylene di-imide dyad was found to undergo a photocyclization reaction upon irradiation with 532 nm laser light, where both the open- and the closed-ring isomers of DAE unit have no absorption band. Wavelength dependence of the photoreaction and oxygen effect revealed that the triplet state is responsible to the photocyclization reaction. Molecular design strategy described in this chapter will help to develop novel photochromic DAEs for advanced molecular probes in biological systems.

Keywords

Diarylethene Visible-light photoreactivity Molecular design Energy transfer Triplet 

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Copyright information

© Springer Japan KK 2017

Authors and Affiliations

  1. 1.Department of Applied Chemistry & Biochemistry, Graduate School of Science & TechnologyKumamoto UniversityKumamotoJapan
  2. 2.Reasearch Center for Smart MoleculesRikkyo UniversityTokyoJapan

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