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Chiral-induced synthesis of chiral covalent organic frameworks core-shell microspheres for HPLC enantioseparation

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Abstract

Two chiral covalent organic frameworks (CCOFs) core-shell microspheres based on achiral organic precursors by chiral-induced synthesis strategy for HPLC enantioseparation are reported for the first time. Using n-hexane/isopropanol as mobile phase, various kinds of racemates were selected as analytes and separated on the CCOF-TpPa-1@SiO2 and CCOF-TpBD@SiO2-packed columns with a low column backpressure (3 ~ 9 bar). The fabricated two CCOFs@SiO2 chiral columns exhibited good separation performance towards various racemates with high column efficiency (e.g., 19,500 plates m−1 for (4-fluorophenyl)ethanol and 18,900 plates m−1 for 1-(4-chlorophenyl)ethanol) and good reproducibility. Some effects have been investigated such as the analyte mass and column temperature on the HPLC enantioseparation. Moreover, the chiral separation results of the CCOF-TpPa-1@SiO2 chiral column and the commercialized Chiralpak AD-H column show a good complementarity. This study demonstrates that the usage of chiral-induced synthesis strategy for preparing CCOFs core-shell microspheres as a novel stationary phase has a good application potential in HPLC.

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Funding

This work is supported by the National Natural Science Foundation of China (Nos. 22364022, 21964021, and 22064020) and the Applied Basic Research Foundation of Yunnan Province (No. 202201AT070029 and 202101AT070101).

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  1. Cheng Liu and Ping Guo contributed equally to this work.

Authors and Affiliations

  1. Department of Chemistry, Yunnan Normal University, Kunming, 650500, People’s Republic of China

    Cheng Liu, Ping Guo, Xiao-Yan Ran, Yu-Lan Zhu, Bang-Jin Wang, Jun-Hui Zhang, Sheng-Ming Xie & Li-Ming Yuan

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Liu, C., Guo, P., Ran, XY. et al. Chiral-induced synthesis of chiral covalent organic frameworks core-shell microspheres for HPLC enantioseparation. Microchim Acta 191, 281 (2024). https://doi.org/10.1007/s00604-024-06347-8

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