Homochiral Self-Sorting During Macrocycle Formation and their Chiroptical Properties.

Several BINOL-derived C2-symmetric aldehydes were synthesized to investigate chiral self-sorting phenomena during macrocycle formation in the presence of aliphatic and aromatic bisamines. While self-sorting was unsuccessful with aliphatic amines, aromatic amine dictated complete homochiral self-sorting, confirmed by H NMR analysis and molecular modelling. Additionally, the impact of macrocyclization on the chiroptical properties of these macrocycles was examined. The Cotton effects band red-shifted for aromatic amines owing to extended conjugation. Notably, a substantial increase in specific rotation was observed upon macrocycle formation.