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Chromatographic Separation of the Enantiomers of a Series of C2-Asymmetric Bi-Naphthyl Compounds by Molecularly Imprinted Polymers

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Abstract

The aim of this study was to observe the chiral separation of a series of C2-asymmetric bi-naphthyl compounds on molecularly imprinted polymers (MIPs) using 1,1′-bi-2-naphthol (BINOL) as template. MIP prepared using 4-vinylpyridine as the functional monomer showed better chiral recognition for the template than the MIPs prepared using acrylamide, 2-(diethylamino)ethylmethacrylate and 2-vinylpyridine, respectively. 1H-NMR was used for comparison of the interactions between template and functional monomers. For chromatographic analysis the effects of mobile phase and temperature on the chiral separation were investigated. When 4-vinylpyridine was employed as the functional monomer, chiral separation of 1,1′-bi-2-naphthol and its analogues were studied. The MIP also demonstrated an ability to discriminate between enantiomers of structurally related compounds that had not been imprinted. The thermodynamic parameters of interactions between substrates and MIP in acetonitrile based mobile phase were investigated by the Van’t Hoff equation. In this study, the specific hydrogen-bonding interactions seemed to be the key factor to achieve chiral separation.

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Acknowledgments

This work was financed by the National Nature Science Foundation of China (No. 20202015) and the Research Foundation for the Doctoral Program of High Education of China (No. 20020558026).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, 510275, People’s Republic of China

    Yong Luo, Lan Liu, Lihong Li & Qinying Deng

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  1. Yong Luo
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  2. Lan Liu
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  3. Lihong Li
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  4. Qinying Deng
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Correspondence to Lan Liu.

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Luo, Y., Liu, L., Li, L. et al. Chromatographic Separation of the Enantiomers of a Series of C2-Asymmetric Bi-Naphthyl Compounds by Molecularly Imprinted Polymers. Chroma 64, 393–397 (2006). https://doi.org/10.1365/s10337-006-0017-5

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  • DOI: https://doi.org/10.1365/s10337-006-0017-5

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