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

被引:101
作者
Xi, Hancheng [1 ,2 ]
Zhang, Zhipeng [1 ,2 ]
Zhang, Weiwei [1 ,2 ]
Li, Mengqi [1 ,2 ]
Lian, Cheng [1 ,2 ]
Luo, Qianfu [1 ,2 ]
Tian, He [1 ,2 ]
Zhu, Wei-Hong [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Key Lab Adv Mat, Inst Fine Chem, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn,Inst Fine Chem,Shanghai Key L, Shanghai 200237, Peoples R China
基金
中国博士后科学基金;
关键词
SCHIFF-BASE; DIARYLETHENE; DESIGN; PHOTOCHROMISM; EQUILIBRIUM; PHOTOCYCLIZATION; DEACTIVATION; TAUTOMERISM; NANOSYSTEMS; MOLECULES;
D O I
10.1021/jacs.9b07357
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:18467 / 18474
页数:8
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