Salicylideneaniline/Dithienylethene Hybrid Molecular Switches: Design, Synthesis, and Photochromism.

J Org Chem

MTA TTK Lendület Functional Organic Materials Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar Tudósok Krt. 2, 1117 Budapest, Hungary.

Published: January 2024

A hybrid molecular switch comprising salicylideneaniline (SA) and dithienylethene (DTE) moieties around a single benzene ring is reported. Due to an interplay between solvent-assisted enol-keto tautomerization in the former moiety and photochromic electrocyclization in the latter, this dithienylbenzene derivative was found to be photoresponsive at room temperature with a thermally stable closed form. The main photoproduct featuring ring-closed DTE and keto-enamine SA structures could be isolated and converted back to the starting material by irradiation with visible light. The optical properties of the potential structures involved in the overall process were characterized by using density functional theory (DFT) calculations in good agreement with the measured data. The reversibility of the conversion could be tuned by the presence of donor and acceptor substituents, while the introduction of the imine in the form of a benzothiazole moiety enabled photochemistry even in nonprotic solvents.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10777402PMC
http://dx.doi.org/10.1021/acs.joc.3c00828DOI Listing

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