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

Planar-chiral pillar[5]arenes 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 )- and (R )-β-D-galactose functionalized pillar[5]arenes [(S )-GP5 and (R )-GP5] exhibit the S and R planar chirality. Furthermore, (S )-GP5 and (R )-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 and R planar chirality of (S )-GP5 and (R )-GP5 still being retained, suggesting GP5 could be as reliable chiral sources to transfer the S and R planar chirality.