?-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles.

ABSTRACT: Planar-chiral pillar[5]arenes bearing ?-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 )-?-D-galactose functionalized pillar[5]arenes [(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.

SUBMITTER: Sun G 

PROVIDER: S-EPMC6869513 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature