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

Guangping Sun; Liangtao Pu; Srikala Pangannaya; Tangxin Xiao; Xiao-Yu Hu; Xiao-Yu Hu; Juli Jiang; Leyong Wang; Leyong Wang

doi:10.3389/fchem.2019.00743

Frontiers in Chemistry (Nov 2019)

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

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

Affiliations

Guangping Sun: Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
Liangtao Pu: State Key Laboratory of Pollution Control and Resource Reuse, School of Environment, Nanjing University, Nanjing, China
Srikala Pangannaya: Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
Tangxin Xiao: School of Petrochemical Engineering, Changzhou University, Changzhou, China
Xiao-Yu Hu: Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
Xiao-Yu Hu: College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing, China
Juli Jiang: Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
Leyong Wang: Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
Leyong Wang: School of Petrochemical Engineering, Changzhou University, Changzhou, China

DOI: https://doi.org/10.3389/fchem.2019.00743
Journal volume & issue: Vol. 7

Abstract

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

Published in Frontiers in Chemistry

ISSN: 2296-2646 (Online)
Publisher: Frontiers Media S.A.
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://journal.frontiersin.org/journal/chemistry

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