Azophotoswitches containing thiazole, isothiazole, thiadiazole, and isothiadiazole

We report a novel class of azophotoswitches incorporating various five-membered heteroaryl units such as thiazole, isothiazole, thiadiazole, and isothiadiazole. These azophotoswitches were developed through an initial screening of 24 compounds using DFT calculations to identify those with the wavele...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-12, Vol.23 (1), p.27-212
Main Authors: Cheruthu, Nusaiba Madappuram, Hashim, P. K, Sahu, Saugata, Takahashi, Kiyonori, Nakamura, Takayoshi, Mitomo, Hideyuki, Ijiro, Kuniharu, Tamaoki, Nobuyuki
Format: Article
Language:English
Subjects:
Irradiation
Isomerization
Light irradiation
Synthesis
Thiadiazoles
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Summary:We report a novel class of azophotoswitches incorporating various five-membered heteroaryl units such as thiazole, isothiazole, thiadiazole, and isothiadiazole. These azophotoswitches were developed through an initial screening of 24 compounds using DFT calculations to identify those with the wavelength of maximum absorption ( λ max ) at a long wavelength. Subsequently, eight selected azophotoswitches were synthesized. Compounds containing both thiazole and isothiazole moieties showed relatively long λ max compared to the other synthesized compounds. These azophotoswitches exhibited reversible isomerization under visible light irradiation at 430 nm, 450 nm, 470 nm ( trans to cis ) and 525 nm ( cis to trans ). Analysis of the X-ray crystal structures of the cis isomer of phenylazo[1,3,4-thiadiazole] exhibited a unique orthogonal geometry. Novel heterocyclic azophotoswitches synthesized in a single step demonstrate sensitivity to visible light.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob01573h