Enantioselective sensing driven by the interplay of point, helical and planar chirality in pillar[5]arene Pseudo[1]catenanes.

ABSTRACT: Chirality plays a central role in molecular recognition, and systems combining multiple, interdependent chiral elements can offer enhanced enantioselectivity. Here we show that covalent tethering of a dihydroxy-pillar[5]arene with meso-2,11-dibromododecanedioate yields diastereomeric pseudo[1]catenanes that combine three stereogenic features: two point chiral centers within the aliphatic linker, a helical chirality (P/M) induced by macrocycle closure, and a planar chirality of the pillararene ring. This system exhibits dynamic stereochemical behaviour involving in/out conformational equilibria, accompanied by inversion of the planar chirality. Using NMR spectroscopy, X-ray diffraction, DFT calculations and circular dichroism, we characterize the structures and dynamics of these macrobicycl

SUBMITTER: Crisafulli D 

PROVIDER: S-EPMC12775507 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature