NIR-Responsive Double Closed-Ring Isomer of a Diarylethene Fused Dimer Synthesized by Stepwise Photochemical and Oxidative Cyclization Reaction.

Authors

Kurumi Satake, Naoto Ootsuki, Kenji Higashiguchi, Kenji Matsuda

Published in

Journal of the American Chemical Society. Mar 07, 2025. Epub Mar 07, 2025.

Abstract

The double closed-ring isomer of a diarylethene fused dimer was synthesized by a combination of photochemical and oxidative cyclization reaction. The double closed-ring isomer of a diarylethene fused dimer has fixed π-conjugation in a rigid planar framework so that this compound has been long-desired. However, with respect to the photocyclization of a diarylethene dimer with strong electronic interaction, the second-step cyclization is known to be suppressed due to fast energy transfer into the closed-ring isomer generated in the first-step photocyclization. In this work, instead of photoisomerization, oxidative isomerization was applied for the second-step cyclization, where the oxidized state spontaneously underwent thermal cyclization by radical coupling at room temperature. The resulting double closed-ring isomer showed NIR absorption, owing to a widely extended π-conjugation throughout the entire molecule. The double closed-ring isomer underwent a ring-opening reaction forming the closed-open-ring isomer when exposed to NIR light despite having a very low quantum yield of approximately 10^-8. As a result, the fused dimer exhibits reversible stepwise switching induced by photo- and redox stimuli in the UV-vis-NIR region.

PMID:
40053870
Bibliographic data and abstract were imported from PubMed on 08 Mar 2025.

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