Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers

Overview

Journal JACS Au

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Nov 29

PMID 39610732

Authors

Tian-Jiao Han

Qiu-Le Yang

Jiaen Hu

Min-Can Wang

Guang-Jian Mei

Affiliations

Soon will be listed here.

Abstract

The development of chiroptical molecular switches for chiral sensing, data communication, optical displays, chiral logic gates, and asymmetric catalysis is currently a vibrant frontier of science and technology. Herein, we report a practical artificial dynamic system based on a 1,2-diaxial atropisomer. Organocatalytic parallel kinetic resolution allows the divergent synthesis of two sets of stereoisomers with vicinal C-C and N-N axes from the same racemic single-axis substrates. By simply varying the configuration of the single catalyst, all four stereoisomers are accessible. The successive conduction of covalent unlocking/locking and thermal-isomerization processes enables sequential switching between all four atropisomeric states with electronic circular dichroism signal reversal, providing an example of multistate chiroptical molecular switches.

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