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Synthesis and characterization of macroporous silica modified with optically active poly[N-(oxazolinylphenyl)acrylamide] derivatives for potential application as chiral stationary phases

Authors

  • Y. Tian,

    1. Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
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  • W. Lu,

    1. Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
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  • Y. Che,

    1. Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
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  • L. B. Shen,

    1. Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
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  • L. M. Jiang,

    Corresponding author
    1. Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
    • Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
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  • Z. Q. Shen

    1. Key Laboratory of Macromolecule Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, China 310027
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Abstract

Enantiopure acrylamide derivatives, (S)-N-[o-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamide and (R)-N-[o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamide, were synthesized through the acylation of chiral 2-oxazolinylanilines. The radical polymerization of the chiral monomers was carried out with (3-mercaptopropyl)trimethoxysilane as a chain-transfer agent to obtain the corresponding optically active prepolymers with a trimethoxysilyl group. By immobilizing the prepolymers on porous silica gel via the grafting-to method, we prepared a new chiral stationary phase (CSP) and characterized it by elemental analysis, thermogravimetry, and Fourier transform infrared spectroscopy. The enantioseparation capacities of the CSPs were evaluated with high-performance liquid chromatography toward several racemic compounds, including 1,1′-bi-2-naphthol, benzoin, 2-amino-1-butanol, and loxoprofen sodium under the normal-phase mode. The results indicate that the CSPs exhibited improved chromatographic performances compared to their brush-type analogs obtained by the alternative grafting-from approach. Also, the column packed with poly{(R)-N-[o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamide}-bonded silica was found to have an extent of enantioselectivity in the chiral resolution of some unmodified amino acids with reversed-phase eluents. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010

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