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All-Visible-Light-Activated Dithienylethenes Induced by Intramolecular Proton Transfer.

Authors :
Xi H
Zhang Z
Zhang W
Li M
Lian C
Luo Q
Tian H
Zhu WH
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2019 Nov 20; Vol. 141 (46), pp. 18467-18474. Date of Electronic Publication: 2019 Nov 08.
Publication Year :
2019

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.

Details

Language :
English
ISSN :
1520-5126
Volume :
141
Issue :
46
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
31656065
Full Text :
https://doi.org/10.1021/jacs.9b07357