期刊
POLYMER INTERNATIONAL
卷 64, 期 8, 页码 1037-1044出版社
WILEY-BLACKWELL
DOI: 10.1002/pi.4884
关键词
cellulose phenylcarbamate; ionic liquid; partial substitution; chiral recognition
资金
- National Science Foundation of China [51103167, 21174151, 51425307]
Homogeneous carbanilation of cellulose with nine kinds of substituted phenyl isocyanates, in which the substituents were varied from electron-donating to electron-withdrawing groups, was carried out in 1-allyl-3-methylimidazolium chloride (AmimCl) without any catalyst. The degree of substitution (DS) of cellulose phenylcarbamates in a range from 0 to 3 was readily controlled by altering reaction temperature, reaction time and molar ratio of phenyl isocyanate/anhydroglucose unit. Furthermore, the electronic effect of the substituents on the aromatic ring had a prominent impact on the reactivity of phenyl isocyanates. The phenyl isocyanates with stronger electron-withdrawing substituents exhibited a higher reactivity. A plot of DS and Hammett substituent constants exhibited linearity with a positive slope. Subsequently, four kinds of partially substituted cellulose phenylcarbamates with DS of 2.0 were synthesized successfully in AmimCl, and then employed as coated-type chiral stationary phases (CSPs) for high-performance liquid chromatography. The enantioseparation results demonstrated that these CSPs exhibited high chiral recognition abilities for some racemates. The substituents on the phenyl moieties had a considerable effect on the chiral recognition ability of cellulose phenylcarbamate-based CSPs. (c) 2015 Society of Chemical Industry
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