Preparation and Chiral Recognition Ability of Crystalline Cellulose Phenylcarbamate
摘要 As one of the most popular polysaccharide derivatives with high chiral recognition ability,cellulose tris(3,5-dimethylphenylcarbamate)(CDMPC)has been successfully applied in the enantioseparation of a wide range of racemates for various purposes.However,the derivative is usually synthesized with an amorphous structure,and its effect on enantioseparation ability remains obscure.To obtain a better understanding of the correlation between its structure and enantioseparation ability,in this study,CDMPC derivatives with crystalline and amorphous struc-tures were prepared through carbamoylation followed by anti-solvent precipitation.Their chiral recognition abilities were evaluated using high-performance liquid chromatography(HPLC)with chiral stationary phases(CSPs).Interestingly,the ordered arrangement of the helical polymer chains of CDMPC was effectively induced by the aromatic solvent after derivatization,forming a crystalline derivative(c-CDMPC)with a uniform and compact worm-like morphology,whereas the amorphous derivative(a-CDMPC)was obtained by regular treatment with a polar alcoholic solvent.The c-CDMPC-based CSP exhibited higher chiral recognition abilities with much shorter retention times for most racemates in this study,compared to the a-CDMPC-based CSP.In particular,flavanone(Rac-7),an important chiral drug with anti-inflammatory,anti-tumor,and cardiovascular protective activities,was even better resolved with higher enantioselectivity on crystalline c-CDMPC than on Chiralcel OD,a com-mercialized chiral column based on CDMPC.This indicates that the crystalline ordered arrangement played a critical role in the chiral recognition ability of the cellulose derivative.
刊 名 高分子科学(英文版) ISTICEISCI
年,卷(期): 2026, 44(9)
机标分类号: TF123 TQ353.425 TM842
在线出版日期: 2026年10月16日