Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers
Tian-Jiao Han1, Qiu-Le Yang1, Jiaen Hu1
1College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
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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