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Fast UHPLC enantioseparation of liquid crystalline materials with chiral center based on octanol in reversed-phase and polar organic mode

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Abstract

Fast baseline enantioseparation of twenty racemic liquid crystalline compounds was carried out via ultra-performance liquid chromatography through direct enantioseparation in polar organic and reversed-phase modes. Tris(3-chloro-5-methyl-phenylcarbamate) derivative of amylose was used as chiral stationary phase; the chiral selector was covalently immobilized on sub-2 µm silica particles. Experiments were done using either pure acetonitrile as mobile phase or simple binary mobile phases consisting of acetonitrile/water mixtures in different volume ratios. No buffers or additives were used. Studied materials are a set of structurally similar compounds comprising two different structures of chiral center, various length of alkoxy spacer and four patterns of lateral substitution of aromatic core by fluorine. The compounds do not contain any ionizable group. The effect of the enantiomer structure on the retention and enantioseparation was evaluated. Flow rate and column temperature were optimized as part of method development.

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Acknowledgements

The authors gratefully acknowledge financial support from Czech Science Foundation [Project No. CSF 20-19655S], Charles University [Project No. SVV260560] and Operational Programme Research, Development and Education financed by European Structural and Investment Funds and the Czech Ministry of Education, Youth and Sports [Project No. SOLID21-CZ.02.1.01/0.0/0.0/16_019/0000760].

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Authors and Affiliations

  1. Department of Analytical Chemistry, Faculty of Science, Charles University, Prague, Czech Republic

    Petra Vaňkátová, Tereza Šrolerová & Anna Kubíčková

  2. Institute of Physics of the Czech Academy of Sciences, Prague, Czech Republic

    Petra Vaňkátová

  3. Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Prague, Czech Republic

    Květa Kalíková

Authors
  1. Petra Vaňkátová
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  2. Tereza Šrolerová
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  3. Anna Kubíčková
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  4. Květa Kalíková
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Correspondence to Anna Kubíčková.

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Vaňkátová, P., Šrolerová, T., Kubíčková, A. et al. Fast UHPLC enantioseparation of liquid crystalline materials with chiral center based on octanol in reversed-phase and polar organic mode. Monatsh Chem 151, 1235–1240 (2020). https://doi.org/10.1007/s00706-020-02622-5

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  • DOI: https://doi.org/10.1007/s00706-020-02622-5

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