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Evaluation and comparison of N-cycloalkylformylated chitosan bis(arylcarbamate)s as chiral selectors for enantioseparation

Abstract

In order to systematically investigate the structural dependence on the properties of N-cycloalkylformylated chitosan bis(arylcarbamate)s, 3,5-dimethylphenylcarbamates of N-cyclopropylformylated, N-cyclobutylformylated, N-cyclopentylformylated and N-cyclohexylformylated chitosans were prepared as chiral selectors in the present study. Since both the molecular weight of chitosan and the substituents at 3- and 6-positions of the phenylcarbamates are identical, the influences of the substituent at 2-position on solvent tolerability and enantioseparation performance of the chiral selectors were specifically compared and discussed. It was found that solvent tolerability and enantioseparation performances of the chiral selectors obviously differed with the variation of the substituent at 2-position of glucosamine skeleton. Although all the chiral selectors generally showed satisfactory tolerability in ethyl acetate and acetone, the chiral selector with three-membered ring possessed much more preferable tolerability against tetrahydrofuran than the others with four-, five- or six-membered ring. Enantioseparation results revealed that most of the chiral selectors exhibited powerful chiral recognition and enantioseparation abilities, and the chiral selector with five-membered ring possessed the best enantioseparation performance. The correponding coated-type chiral stationary phases prepared from these chitosan-based chiral selectors were able to be complementary with each other and applied as promising chiral separation materials for enantiomeric separations.

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Publication details

The article was received on 11 May 2017, accepted on 05 Aug 2017 and first published on 07 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ01611E
Citation: New J. Chem., 2017, Accepted Manuscript
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    Evaluation and comparison of N-cycloalkylformylated chitosan bis(arylcarbamate)s as chiral selectors for enantioseparation

    Z. Bai, F. Yang, K. Fu, X. Wang, J. Liu, W. Chen, S. Huang and S. Tang, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ01611E

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