Critical Role of Achiral Guest Molecules in Planar Chirality Inversion of Alanine-Appended Pillar[5]arenes

Abstract

Planar chirality inversion of pillar[5]arenes bearing D- or L-alanine substituents on both rims was investigated upon addition of guest molecules having pyridinium or imidazole moieties and long alkyl chains. The D- and L-alanine-substituted pillar[5]arenes exhibited pS and pR planar chirality, respectively. However, this planar chirality was inverted upon inclusion of certain achiral molecules, comprising pyridinium or imidazole moieties and long alkyl chains with terminal hydroxyl or methyl groups.