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Holding of planar chirality of pillar[5]arene by kinetic trapping using host–guest interactions with achiral guest solvents

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Abstract

We report a solvent-dependent switching and holding of planar chirality of pillar[5]arene with stereogenic carbons at both rims by host–guest complexation with achiral guest solvents. The planar chirality could be held for a given length of time at 25 °C in long linear guest solvents by kinetic trapping through host–guest complexation. The kinetic trapping worked at 25 °C, but not at 60 °C, thus a planar-chiral inversion using kinetic trapping based on host–guest complexation in the long linear solvents was demonstrated.

Graphical abstract: Holding of planar chirality of pillar[5]arene by kinetic trapping using host–guest interactions with achiral guest solvents

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Article information


Submitted
12 May 2020
Accepted
15 Jun 2020
First published
15 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Holding of planar chirality of pillar[5]arene by kinetic trapping using host–guest interactions with achiral guest solvents

Y. Nagata, M. Suzuki, Y. Shimada, H. Sengoku, S. Nishida, T. Kakuta, T. Yamagishi, M. Suginome and T. Ogoshi, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03413D

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