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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.

SUBMITTER: Wang H

PROVIDER: S-EPMC8386666 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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

Wang Haiying H Yang Weiwei W Baldridge Kim K KK Zhan Cai-Hong CH Thikekar Tushar Ulhas TU Sue Andrew C-H AC

Chemical science 20210727 33

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 op ...[more]

PMID: 34522295

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