Chirality Induction and Memory of Pillar[4]arene[1]quinone Derivatives in Visible-Light Range.

Abstract

Pillar[4]arene[1]quinone derivatives (PQXs) were synthesized by the oxidation of pillar[5]arenes, which exhibited notable charge transfer (CT) transitions at approximately 485 nm. Successful chiral resolution of two pairs of enantiomeric conformers was achieved. Despite reduced binding affinity, PQXs demonstrated slower racemization kinetics. Visible-light chiroptical induction with a significant dissymmetry factor was attained by complexing PQXs with a chiral guest. The induced enantiomeric excess could be maintained through competitive binding with an achiral guest, offering a promising strategy for chiral sensing and memory.