Journal
ANALYTICA CHIMICA ACTA
Volume 1073, Issue -, Pages 90-98Publisher
ELSEVIER
DOI: 10.1016/j.aca.2019.04.071
Keywords
Chiral separation; Chiral recognition mechanism; Chiral stationary phases; Cellulose mixed esters; Regioselective substitution
Categories
Funding
- National Natural Science Foundation of China [51103167, 51573196, 51425307, 51773210]
- Innovative Research Team Program of Beijing Academy of Science and Technology [IG2016 05 N/C1]
- Youth Innovation Promotion Association CAS [2018040]
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It is challenging to design and fabricate new and high-performance cellulose-based chiral stationary phases (CSPs), due to the indistinct chiral recognition mechanism and the inherent difficulty to control the structure of cellulose derivatives. Herein, taking advantage of the high regioselective benzoylation of cellulose in 1-allyl-3-methylimidazolium chloride, a series of regioselectively substituted cellulose mixed esters, cellulose 6-benzoate-2,3-phenylcarbamate, are directly obtained by a facile two-steps route without protecting and deprotecting process. The resultant cellulose mixed esters exhibit high chiral recognition capability. In particular, when the benzoate group has an electron-donating substituent on phenyl ring, such as 4-tert-butyl group, the corresponding regioselectively substituted cellulose mixed esters have much better enantioseparation capability than cellulose tri(3,5-dimethylphenylcarbamate), which is commercially available as Chiralcel OD column, one of the most powerful CSPs. More importantly, via adjusting the chemical structure of cellulose derivatives and adding a post-treatment process to optimize their chiral recognition properties, the chiral recognition mechanism is clearly revealed. The synergy of the hydrophobic helical conformation, weak hydrogen-bond donating ability and appropriate distribution of substituents of cellulose derivatives is essential to fabricate high-performance CSPs. (C) 2019 Elsevier B.V. All rights reserved.
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