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Phenylazothiazoles as Visible-Light Photoswitches

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Title: Phenylazothiazoles as Visible-Light Photoswitches
Authors: Lin, Runze Browse this author
Hashim, P. K. Browse this author
Sahu, Saugata Browse this author
Amrutha, Ammathnadu S. Browse this author
Cheruthu, Nusaiba Madappuram Browse this author
Thazhathethil, Shakkeeb Browse this author
Takahashi, Kiyonori Browse this author
Nakamura, Takayoshi Browse this author
Kikukawa, Takashi Browse this author
Tamaoki, Nobuyuki Browse this author →KAKEN DB
Issue Date: 12-Apr-2023
Publisher: American Chemical Society
Journal Title: Journal of the American Chemical Society
Volume: 145
Issue: 16
Start Page: 9072
End Page: 9080
Publisher DOI: 10.1021/jacs.3c00609
Abstract: A novel class of photoswitches based on a phenylazothiazole scaffold that undergoes reversible isomerization under visible-light irradiation is reported. The photoswitch, which comprises a thiazole heteroaryl segment directly connected to a phenyl azo chromophore, has very different spectral characteristics, such as a redshifted absorption maximum wavelength and wellseparated absorption bands of the trans and cis isomers, than conventional azobenzene and other heteroaryl azo compounds. Substituents at the ortho and para positions of the phenyl ring of the photoswitch resulted in a further shift to longer wavelengths up to 525 nm at the absorption maximum with a small thermal stability compensation. These photoswitches showed excellent photostationary distributions of the trans and cis isomers, thermal half-lives of up to 7.2 h, and excellent reductant stability. The X-ray crystal structure analysis revealed that the trans isomers exhibited a planar geometry and the cis isomers exhibited a T-shaped orthogonal geometry. Detailed ab initio calculations further demonstrated the plausible electronic transitions and isomerization energy barriers, which were consistent with the experimental observations. The fundamental design principles elucidated in this study will aid in the development of a wide variety of visible-light photoswitches for photopharmacological applications.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
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Type: article
Appears in Collections:電子科学研究所 (Research Institute for Electronic Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 玉置 信之

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