Spontaneous and induced chiral symmetry breaking of stereolabile pillar[5]arene derivatives upon crystallisation. Issue 33 (27th July 2021)

• Record Type: Journal Article
• Authors: Wang, Haiying; Yang, Weiwei; Baldridge, Kim K.; Zhan, Cai-Hong; Thikekar, Tushar Ulhas; Sue, Andrew C.-H.
• Is Part Of: Chemical science. Volume 12:Issue 33(2021)
• Page Start: 10985
• Page End: 10989
• Publication Date: 2021-07-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc02560k
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Stereolabile pillar[5]arene 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. 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.