A hydroxyl-functionalized homochiral porous organic cage for gas chromatographic separations
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ORIGINAL PAPER
A hydroxyl-functionalized homochiral porous organic cage for gas chromatographic separations Hong-Xing Li 1 & Tian-Peng Xie 1 & Ke-Qian Yan 1 & Sheng-Ming Xie 1 & Bang-Jin Wang 1 & Jun-Hui Zhang 1 Li-Ming Yuan 1
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Received: 24 December 2019 / Accepted: 31 March 2020 # Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract A hydroxyl-functionalized homochiral porous organic cage (POC) was synthesized and characterized by FTIR, NMR, thermogravimetric analysis (TGA), MALDI-TOF-MS, and elemental analysis. The synthesized homochiral POC was used as stationary phase to prepare a capillary gas chromatography (GC) column by a static coating method. The fabricated column shows excellent selectivity not only for the separation of positional isomers but also for the resolution of various racemates. Thirty-nine racemates have been resolved on the column, including alcohols, diols, halohydrocarbons, epoxides, esters, lactones, ketones, ethers, and organic acids. Compared to the commercial β-DEX 120 column and previously reported chiral POCs (CC3-R, CC9, and CC10)coated columns, there are 11, 10, 24, and 15 tested racemates that cannot be resolved on β-DEX 120 column, CC3-R column, CC9 column, and CC10 column, respectively. This reveals that the fabricated column has prominent complementarity or superior separation performance to these columns in enantioseparation. Besides, the fabricated column can achieve some enantioseparations which are not possible using all previously reported chiral POC-based columns. Some positional isomers (xylenes, dichlorobenzenes, dibromobenzenes, nitrochlorobenzenes, and nitrobromobenzenes) were also separated with high-resolution values. The column exhibits good repeatability, reproducibility, and stability. The relative standard deviation (RSD) values of retention times were 0.03–0.18%, 0.11–0.92%, and 2.1–6.6% for run-to-run (n = 5), day-today (n = 5), and column-to-column (n = 3), respectively. The experimental results demonstrate the great potential of POCs for practical application in GC. Keywords Porous organic cage . Chiral stationary phase . Capillary column . Gas chromatography . Chiral separation . Racemates . Positional isomers
Introduction Many fields such as chemistry, biomedicine, pharmaceutical industry, agriculture, and food science involve chirality [1]. A chiral compound has two or more enantiomers. Enantiomers
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00604-020-04252-4) contains supplementary material, which is available to authorized users. * Jun-Hui Zhang [email protected] * Li-Ming Yuan [email protected] 1
Department of Chemistry, Yunnan Normal University, Kunming 650500, People’s Republic of China
show identical nonchiroptic physical and chemical properties in an achiral environment, but they may exhibit different stereoselectivities in a chiral environment. For example, chiral molecules, especially chiral drugs, often exhibit distinct biological and pharmacological activities in li
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