Issue 7, 2021

Trace mild acid-catalysed ZE isomerization of norbornene-fused stilbene derivatives: intelligent chiral molecular photoswitches with controllable self-recovery

Abstract

Stilbene derivatives have long been known to undergo “acid-catalyzed” ZE isomerization, where a strong mineral acid at high concentration is practically necessary. Such severe reaction conditions often cause undesired by-reactions and limit their potential application. Herein, we present a trace mild acid-catalyzed ZE isomerization found with stilbene derivatives fused with a norbornene moiety. By-reactions, such as the migration of the C[double bond, length as m-dash]C double bond and electrophilic addition reactions, were completely inhibited because of the ring strain caused by the fused norbornene component. Direct photolysis of the E isomers at selected wavelengths led to the EZ photoisomerization of these stilbene derivatives and thus constituted a unique class of molecular switches orthogonally controllable by light and acid. The catalytic amount of acid could be readily removed, and the ZE isomerization could be controlled by turning on/off the irradiation of a photoacid, which allowed repeated isomerization in a non-invasive manner. Moreover, the Z isomer produced by photoisomerization could spontaneously self-recover to the E isomer in the presence of a catalytic amount of acid. The kinetics of ZE isomerization were adjustable by manipulating catalytic factors and, therefore, unprecedented molecular photoswitches with adjustable self-recovery were realized.

Graphical abstract: Trace mild acid-catalysed Z → E isomerization of norbornene-fused stilbene derivatives: intelligent chiral molecular photoswitches with controllable self-recovery

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Sep 2020
Accepted
28 Dec 2020
First published
28 Dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 2614-2622

Trace mild acid-catalysed ZE isomerization of norbornene-fused stilbene derivatives: intelligent chiral molecular photoswitches with controllable self-recovery

T. Hao, Y. Yang, W. Liang, C. Fan, X. Wang, W. Wu, X. Chen, H. Fu, H. Chen and C. Yang, Chem. Sci., 2021, 12, 2614 DOI: 10.1039/D0SC05213B

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