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Synthesis of a chiral stationary phase with poly[styrene-b-cellulose 2,3-bis(3,5-dimethylphenylcarbamate)] by surface-initiated atom transfer radical polymerization and its chiral resolution efficiency

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Abstract

A chiral stationary phase (CSP) with poly[styrene-b-cellulose 2,3-bis(3,5-dimethylphenylcarbamate)] was synthesized by the surface-initiated atom transfer radical polymerization (SI-ATRP) of cellulose 2,3-bis(3,5-dimethylphenylcarbamate)-6-acrylate after the SI-ATRP of styrene on the surface of silicon dioxide supports in pyridine. The successful preparation of the CSP with poly[styrene-b-cellulose 2,3-bis(3,5-dimethylphenylcarbamate)] was confirmed via Fourier transform infrared spectroscopy, field emission scanning electron microscopy, X-ray photoelectron spectroscopy, elemental analysis, and thermal analysis. The applicability for the chiral resolution of the CSP with poly[styrene-b-cellulose 2,3-bis(3,5-diphenylcarbamate)] was evaluated with high-performance liquid chromatography with 10 racemates under various mobile phases of hexane/alcohol, hexane/tetrahydrofuran (THF), and hexane/chloroform. The results show that the CSP with poly[styrene-b-cellulose 2,3-bis(3,5-diphenylcarbamate)] could be used in THF and chloroform as eluents. The chiral resolutions of the commercial Chiracel OD, the CSP with cellulose 2,3-bis(3,5-dimethylphenylcarabmate), and the CSP with poly[styrene-b-cellulose 2,3-bis(3,5-dimethylphenylcarbamate)] prepared by SI-ATRP were examined. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

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