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Updated: Jan 5, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
All-Visible-Light-Activated Dithienylethenes Induced by Intramolecular Proton Transfer
Hancheng Xi1, Zhipeng Zhang1, Weiwei Zhang1
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering , East China University of Science & Technology , Shanghai 200237 , China.
Abstract:
The fast light-responsive dithienylethenes (DTEs) are one of the most attractive photochromic families because of their excellent thermal irreversibility and fatigue resistance. However, the all-visible-light-activated DTE system still remains challenging because most of them require the harmful high-energy ultraviolet light to trigger their photocyclization reaction. Here, we have for the first time borrowed a specific intramolecular proton transfer (IPT) process and rationally designed a series of all-visible-light-driven DTEs. Incorporating the IPT-functional group to DTE unit gives rise to an extra absorption band with a distinct red shift, which enables the photocyclization of DTEs under stimuli of visible light at 450 nm, as well as ensuring the desirable photoswitching efficiency. The isomerization from OH form to NH form induced by IPT can decrease the energy gap for excitation and photocyclization, thereby affording the all-visible-light-triggered photochromic performance, which can not only work well in a polar solvent system but also show its effectiveness in polymeric gel systems. In this regard, we can provide a general and reliable platform to construct all-visible-light-driven DTEs with excellent reversible photoswitching and broad applicability, especially with avoiding the use of harmful ultraviolet light to induce their photocyclization.
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