β-D-Galactose-Functionalized Pillar5arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles

Planar-chiral pillar5arenes bearing β-D-galactose substituents on both rims have been successfully synthesized and effectively separated by silica gel chromatography with a high yield. The obtained (S p )- and (R p )-β-D-galactose functionalized pillar5arenes (S p-D )-GP5 and (R p-D )-GP5 exhibit the S p and R p planar chirality. Furthermore, (S p-D )-GP5 and (R p-D )-GP5 can not racemize according to dynamic 1H NMR and CD spectra. Notably, GP5 is able to capture a guest molecule (DNS-CPT) to form a host-guest supramolecular amphiphile, which can further self-assemble into chiral nanoparticles with the S p and R p planar chirality of (S p-D )-GP5 and (R p-D )-GP5 still being retained, suggesting GP5 could be as reliable chiral sources to transfer the S p and R p planar chirality.