Membrane separation of enantiomers

We investigated various approaches to enhance chiral recognition and selectivity of polymers for membrane-based enantioseparation. Our recent advances include blending polymers with different ionic liquids to improve chiral recognition by tuning the polymer structure, optimizing membrane preparations and conditions of enantioseparation process for new synthesized optically active linear polyimides and hyperbranched poly(amic acid–imide). We also tested and optimized ionically bound cyclodextrin derivatives to Nafion^®, where membranes showed great potential for electrostatic binding and enantioseparation of chiral drugs. Furthermore, we reviewed the progress in microfluidics and micromembrane separations, highlighting their potential for the continuous production of pure enantiomers. Theoretical analysis of lateral electrochromatography offers an insight into operational parameters necessary for efficient separation of enantiomers in the presence of the electric field. The molecular dynamics simulations are regularly employed to answer the interplay of molecular structures of the solvent/chiral selector/target chiral molecule.

Chiral selector β-cyclodextrin containing spacer modifying binding site to Nafion. Variable topology of complexes of β-cyclodextrin and (R)-ibuprofen. Scheme of pertraction cell for enantioseparation

Hovorka Š., Hrdlička Z., Jeništová A., Švecová M., Izák P., Čížek J., Michalcová A., Hadravová R., Vopička O.: Impacts of ions on the plasticization of cellulose triacetate by fluorinated ionic liquids: Thermal properties, microscopy, Raman spectra, and sorption of pure enantiomers. Polymer 290(5 Jan), 126502, 2024. DOI
Sysel P., Holakovský R., Hovorka Š., Žádný J., Izák P.: Preparation of Optically Active Polyimides Based on 2,2´-diamino-1,1´-binaphthalene. J. Polym. Mater. 39(3-4), 325-335, 2023. DOI
Petrusova Z., Slouka Z., Vobecka L., Polezhaev P., Hasal P., Pribyl M., Izak P.: Microreaction and membrane technologies for continuous single-enantiomer production: A review. Cat. Rev. 65(3), 773-821, 2023. DOI
Sysel P., Hovorka S., Kohout M., Holakovsky R., Zadny J., Cizek J., Izak P.: Optically active polyimides with different thermal histories of their preparation. Chirality 34(8), 1151-1161, 2022. DOI
Přibyl M., Izák P., Slouka Z.: A mathematical model of a lateral electrochromatography device for continuous chiral separation. Sep. Purif. Technol. 282(1 Feb), 120033, 2022. DOI
Hercikova J., Spalovska D., Fruhauf P., Izak P., Lindner W., Kohout M.: Design and synthesis of naphthalene-based chiral strong cation exchangers and their application for chiral separation of basic drugs. J. Sep. Sci. 44(18), 3348-3356, 2021. DOI
Kasal P., Michel M., Gaalova J., Curinova P., Izak P., Dian J., Jindrich J.: Chiral Nafion membranes prepared by strong electrostatic binding of multiply positively charged beta-cyclodextrin derivatives for tryptophan racemic mixtures’ separation. Mater. Today Commun. 27(Jun), 102234, 2021. DOI
Gaalova J., Michel M., Bourassi M., Ladewig B. P., Kasal P., Jindrich J., Izak P.: Nafion membranes modified by cationic cyclodextrin derivatives for enantioselective separation. Sep. Purif. Technol. 266(1 Jul), 118538, 2021. DOI
Brozova L., Zazpe R., Otmar M., Prikryl J., Bulanek R., Zitka J., Krejcikova S., Izak P., Macak J. M.: Chiral Templating of Polycarbonate Membranes by Pinene Using the Modified Atomic Layer Deposition Approach. Langmuir 36(42), 12723-12734, 2020. DOI
Skvara J., Nezbeda I., Izak P.: Molecular dynamics study of racemic mixtures. II. Temperature dependence of the separation of ibuprofen racemic mixture with beta-cyclodextrin in methanol solvent. J. Mol. Liq. 302(15 Mar), 112575, 2020. DOI
Nezbeda I., Škvára J.: On industrial applications of molecular simulations. Mol. Simul. 47(10-11), 846-856, 2020. DOI
Gaalova J., Yalcinkaya F., Curinova P., Kohout M., Yalcinkaya B., Kostejn M., Jirsak J., Stibor I., Bara J. E., Van der Bruggen B., Izák P.: Separation of racemic compound by nanofibrous composite membranes with chiral selector. J. Membr. Sci. 596(15 Feb), 117728, 2020. DOI
Otmar M., Gaalova J., Zitka J., Brozova L., Curinova P., Kohout M., Hovorka S., Bara J. E., Van der Bruggen B., Jirsak J., Izák P.: Preparation of PSEBS membranes bearing (S)-(-)-methylbenzylamine as chiral selector. Eur. Polym. J. 122(5 Jan), 109381, 2020. DOI
Kohout M., Hovorka S., Hercikova J., Wilk M., Sysel P., Izak P., Bartunek V., von Baeckmann C., Picha J., Fruhauf P.: Evaluation of silica from different vendors as the solid support of anion-exchange chiral stationary phases by means of preferential sorption and liquid chromatography. J. Sep. Sci. 42(24), 3653-3661, 2019. DOI
Škvára J., Nezbeda I.: Molecular dynamics study of racemic mixtures: Solutions of ibuprofen and β-cyclodextrin in methanol. J. Mol. Liq. 265(1 Sep), 791-796, 2018. DOI
Curinova P., Dracinsky M., Jakubec M., Tlusty M., Janku K., Izak P., Holakovsky R.: Enantioselective complexation of 1-phenylethanol with chiral compounds bearing urea moiety. Chirality 30(6), 798-806, 2018. DOI