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  • Title: [Homogeneous synthesis of cellulose phenylcarbamates and evaluation of their enantioseparation capabilities].
    Author: Yin C, Yang T, Zhang J, Zhang J.
    Journal: Se Pu; 2020 Apr 08; 38(4):476-483. PubMed ID: 34213231.
    Abstract:
    Understanding the structure-property relationship of polysaccharide derivatives is of great significance toward the development of novel chiral stationary phases. In this work, we used an ionic liquid, 1-allyl-3-methylimidazolium chloride (AmimCl), as the solvent and introduced phenyl isocyanates with various substituents into cellulose to obtain a series of cellulose phenylcarbamates. The effects of the degree of substitution (DS), as well as the type and position of the substituents, on the chiral separation capability of the cellulose phenylcarbamates were researched in detail. With an increase in the DS, the chiral recognition capability of the cellulose phenylcarbamates improved dramatically for most of the chiral analytes. Fully substituted cellulose phenylcarbamates showed the best enantioseparation capabilities. In addition, the type and position of the substituents on the benzene ring significantly influenced the chiral separation capabilities of the cellulose phenylcarbamates. Cellulose 3-methyl-4-chlorophenylcarbamate, 3,5-dichlorophenylcarbamate, and 2-methyl-5-chlorophenylcarbamate had better chiral recognition capabilities than cellulose 3,5-dimethylphenylcarbamate for some chiral analytes.
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