A Chiral Porous Organic Polymer Used as the Stationary Phase for High-Resolution Gas Chromatography Separations

Abstract

A chiral porous organic polymer (cPOP) was synthesized through nucleophilic substitution polymerization between dichloromaleimide and aromatic amine. This cPOP was used as a new chiral stationary phase (CSP) for gas chromatography (GC) chiral separation. In this work, we first used this cPOP as the CSP for gas chromatography to investigate its ability to separate racemic mixtures, including amino acid derivatives, chiral alcohols, aldehydes, alkanes, ketones, esters, and organic acids. The results showed that the column can effectively separate various racemic mixtures and achieve baseline separation of threonine (Rs = 1.91). Furthermore, the separation mechanism was elucidated by density functional theory (DFT) simulation. Additionally, the cPOP column demonstrated good repeatability and stability. The relative standard deviations (RSDs) for intraday were 0.11%–0.12% (n = 3) for the retention time of n-butyl glycidyl ether, 0.1%–0.34% (n = 3) for interday, and 2.25%–3.37% (n = 3) for column to column. This work shows that cPOP has good potential as chiral stationary phases in gas chromatography.