Enantiospecific photoresponse of sterically hindered diarylethenes for chiroptical switches and photomemories

Scientific Reports
Wenlong LiHe Tian

Abstract

Light-driven transcription, replication and enzyme catalysis are critically dependent upon a delicate transfer between molecular and supramolecular chirality. Chemists have well realized the impressive stereospecificity over many thermally accessible cycloaddition with chiral catalysts, but making light work in the enantiomer control of diarylethene photocyclization has proved to be more challenging. Here, we report a unique sterically hindered diarylethene (BBTE) system with absolute enantiospecific photocyclization and cycloreversion. Moreover, we have fully separated all the five thermally stable isomers, consisting of one achiral parallel conformer, one pair of anti-parallel ring-open enantiomers, and another pair of ring-closed enantiomers, whose absolute chiral configurations are entirely elucidated by single X-ray crystallographic analyses. The photo-responsive feature exhibits a reversible, complete enantio-control transformation without racemism, offering an unrivaled unimolecular enantiospecific platform for potential applications as bistable chiroptical switches and all-photonic photomemories with optical rotation as non-destructive readout.

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Citations

Jun 15, 2016·Scientific Reports·Luyang ZhaoJianzhuang Jiang
Jan 18, 2017·The Journal of Organic Chemistry·Andrey G LvovValerii Z Shirinian
Oct 8, 2015·Nanoscale·Yuanlin ZhangAlexander D Q Li
Nov 15, 2016·Chemical Communications : Chem Comm·Tian-Guang ZhanKang-Da Zhang
Jun 30, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Li-Xuan CaiQing-Fu Sun
Jul 18, 2015·Angewandte Chemie·Juyoung Yoon, A Prasanna de Silva
Jun 23, 2015·Chemistry, an Asian Journal·Ruiji LiTsuyoshi Kawai
Dec 18, 2020·Chemical Communications : Chem Comm·Susnata PramanikIvan Huc
Oct 14, 2017·Journal of the American Chemical Society·Nathan Man-Wai WuVivian Wing-Wah Yam
Aug 2, 2018·Journal of the American Chemical Society·Prince RavatMichal Juríček
Feb 28, 2019·Inorganic Chemistry·Soumalya BhattacharyyaPartha Sarathi Mukherjee
Apr 15, 2020·ACS Applied Materials & Interfaces·Ashish SinghTapas Kumar Maji
May 16, 2019·Journal of the American Chemical Society·Yi QinHai-Bo Yang

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Methods Mentioned

BETA
X-ray
irradiating
circular dichroism
NMR

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