Issue 33, 2021

Spontaneous and induced chiral symmetry breaking of stereolabile pillar[5]arene derivatives upon crystallisation

Abstract

Stereolabile pillar[5]arene (P[5]) derivatives, which are dynamic racemic mixtures in solution on account of their low inversion barriers, were employed as platforms to study chiral symmetry breaking during crystallisation. In the solid state, we showed that crystal enantiomeric excess of a conglomerate-forming P[5] derivative can be obtained by handpicking and Viedma ripening without the intervention of external chiral entities. On the other hand, in the presence of ethyl D/L-lactate as both optically-active solvents and chiral guests, the handedness of P[5] derivative crystals, either forming racemic compounds or conglomerates upon condensation, can be directed and subsequently inverted in a highly controllable manner.

Graphical abstract: Spontaneous and induced chiral symmetry breaking of stereolabile pillar[5]arene derivatives upon crystallisation

Supplementary files

Article information

Article type
Edge Article
Submitted
10 5 2021
Accepted
19 7 2021
First published
27 7 2021
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, 10985-10989

Spontaneous and induced chiral symmetry breaking of stereolabile pillar[5]arene derivatives upon crystallisation

H. Wang, W. Yang, K. K. Baldridge, C. Zhan, T. U. Thikekar and A. C.-H. Sue, Chem. Sci., 2021, 12, 10985 DOI: 10.1039/D1SC02560K

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