Abstract
A chiral stationary phase is proposed on the basis of 3,4,9,10-perylenetetracarboxylic acid (3,4,9,10-perylentetracarbonacid, PTCA). The PTCA molecule itself is not chiral; however, it can form chiral supramolecular structures. Symmetry breaking during the self-assembly of PTCA supramolecular structures was carried out similarly to the Viedma ripening process. The obtained stationary phases with PTCA multilayers on an inert solid support and C18 silica were used to separate racemates in gas and liquid chromatography, respectively. It was found that the proposed stationary phases exhibit enantioselectivity with respect to pairs of enantiomers bearing a hydroxyl group at an asymmetric carbon atom. Enantiomers of butanol-2, pentanol-2, and 1-methoxy-propanol-2 were separated by gas chromatography. The separation of menthols was achieved in the normal-phase HPLC mode. It was shown that the separation of the last named compounds is possible up to a concentration of 0.04 mg/mL inclusive.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS1061934820060106/MediaObjects/10809_2020_1358_Fig1_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS1061934820060106/MediaObjects/10809_2020_1358_Fig2_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS1061934820060106/MediaObjects/10809_2020_1358_Fig3_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS1061934820060106/MediaObjects/10809_2020_1358_Fig4_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS1061934820060106/MediaObjects/10809_2020_1358_Fig5_HTML.gif)
Similar content being viewed by others
REFERENCES
Schurig, V., J. Chromatogr. A, 2001, vol. 906, p. 275.
Venema, A., Henderiks, H., and Geest, R.V., J. High Resolut. Chromatogr., 1991, vol. 14, p. 676.
**e, S.M. and Yuan, L.M., J. Sep. Sci., 2017, vol. 40, no. 1, p. 124.
Adly, F.G., Antwi, N.Y., and Ghanem, A., Chirality, 2016, vol. 28, no. 2, p. 97.
Shapovalova, E.N., Fedorova, I.A., Priporova, A.A., Anan’eva, I.A., and Shpigun, O.A., Analitika Kontrol’, 2016, vol. 20, no. 2, p. 168.
Prokhorova, A.F., Kuznetsov, M.A., Shapovalova, E.N., Staroverov, S.M., and Shpigun, O.A., Moscow Univ. Chem. Bull. (Engl. Transl.), 2010, vol. 65, no. 5, p. 295.
Lebedeva, M.V., Prokhorova, A.F., Shapovalova, E.N., and Shpigun, O.A., Moscow Univ. Chem. Bull. (Engl. Transl.), 2013, vol. 68, no. 5, p. 215.
Ya, H., Two-Dimensional (2D) Functional Molecular Networks, Blunt, M., Ed., London: Univ. College London, 2016.
Meijer, E.W. and Palmans, A.R.A., Angew. Chem., Int. Ed., 2007, vol. 46, p. 8948.
Fujiki, M., Symmetry, 2014, vol. 6, p. 677.
Bruin, A.G.D., Barbour, M.E., and Briscoe, W.H., Polym. Int., 2014, vol. 63, p. 165.
Zhao, L., Liu, M., Li, S., Li, A., An, H., Ye, H., and Zhang, Y.J., J. Mater. Chem. C, 2015, vol. 3, p. 3650.
Godlewski, S. and Szymonski, M., Appl. Surf. Sci., 2011, vol. 258, p. 1300.
Mannsfeld, S., Toerker, M., Scgmitz-Hubsch, T., Sellam, F., Fritz, T., and Leo, K., Org. Electron., 2001, vol. 2, p. 121.
Zhao, Y. and Wang, J., J. Phys. Chem. C, 2017, vol. 121, no. 8, p. 4488.
Sun, X., Jonkman, H.T., and Silly, F., Nanotecnology, 2010, vol. 21, p. 165602.
Gus’kov, V.Yu., Sukhareva, D.A., Arslanova, I.V., and Musabirov, D.E., J. Anal. Chem., 2017, vol. 72, no. 10, p. 1089.
Nafikova, A.R., Allayarova, D.A., and Gus’kov, V.Yu., J. Anal. Chem., 2019, vol. 74, no. 6, p. 565.
Gus’kov, V.Y., Sukhareva, D.A., Gainullina, Y.Y., Hamitov, E.M., Galkin, Y.G., and Maistrenko, V.N., Supramol. Chem., 2018, vol. 30, no. 11, p. 940.
Viedma, C., Phys. Rev. Lett., 2005, vol. 94, 065504.
Davankov, V.A., Symmetry, 2018, vol. 10, p. 749.
Sogutoglu, L.-C., Steendam, R.R.E., Meekes, H., Vlieg, E., and Rutjes, F.P.J.T., Chem. Soc. Rev., 2015, vol. 44, p. 6723.
Gus’kov, V.Yu. and Maistrenko, V.N., J. Anal. Chem., 2018, vol. 73, no. 10, p. 937.
ACKNOWLEDGMENTS
We are grateful to Prof. B. I. Kutepov for the IR spectra of 3,4,9,10-perylenetetracarboxylic acid and for Prof. I. A. Massalimov for the analysis of particle sizes of the modifier.
Funding
This work was supported by the Russian Science Foundation, project no. 17-73-10181.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by V. Kudrinskaya
Rights and permissions
About this article
Cite this article
Gus’kov, V.Y., Gainullina, Y.Y., Uteeva, Z.D. et al. Application of a Chiral Stationary Phase Based on 3,4,9,10-Perylenetetracarboxylic Acid to the Separation of Enantiomers under the Conditions of Gas and Liquid Chromatography. J Anal Chem 75, 778–782 (2020). https://doi.org/10.1134/S1061934820060106
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1061934820060106