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

Pillar[4]arene[1]quinone derivatives ( PQ X s) 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, PQ X s demonstrated slower racemization kinetics. Visible-light chiroptical induction with a significant dissymmetry factor was attained by complexing PQ X s 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.