AUTHOR=Sun Guangping , Pu Liangtao , Pangannaya Srikala , Xiao Tangxin , Hu Xiao-Yu , Jiang Juli , Wang Leyong 

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

JOURNAL=Frontiers in Chemistry

VOLUME=7

YEAR=2019

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2019.00743

DOI=10.3389/fchem.2019.00743

ISSN=2296-2646

ABSTRACT=<p>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 (<italic>S</italic><sub><italic>p</italic></sub>)- and (<italic>R</italic><sub><italic>p</italic></sub>)-β-D-galactose functionalized pillar[5]arenes [(<italic>S</italic><sub><italic>p</italic>-<italic>D</italic></sub>)-<bold>GP5</bold> and (<italic>R</italic><sub><italic>p</italic>-<italic>D</italic></sub>)-<bold>GP5</bold>] exhibit the <italic>S</italic><sub><italic>p</italic></sub> and <italic>R</italic><sub><italic>p</italic></sub> planar chirality. Furthermore, (<italic>S</italic><sub><italic>p</italic>-<italic>D</italic></sub>)-<bold>GP5</bold> and (<italic>R</italic><sub><italic>p</italic>-<italic>D</italic></sub>)-<bold>GP5</bold> can not racemize according to dynamic <sup>1</sup>H NMR and CD spectra. Notably, <bold>GP5</bold> is able to capture a guest molecule (<bold>DNS-CPT</bold>) to form a host-guest supramolecular amphiphile, which can further self-assemble into chiral nanoparticles with the <italic>S</italic><sub><italic>p</italic></sub> and <italic>R</italic><sub><italic>p</italic></sub> planar chirality of (<italic>S</italic><sub><italic>p</italic>-<italic>D</italic></sub>)-<bold>GP5</bold> and (<italic>R</italic><sub><italic>p</italic>-<italic>D</italic></sub>)-<bold>GP5</bold> still being retained, suggesting <bold>GP5</bold> could be as reliable chiral sources to transfer the <italic>S</italic><sub><italic>p</italic></sub> and <italic>R</italic><sub><italic>p</italic></sub> planar chirality.</p>