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为了探讨功能基团对苯甲酰胺基-β-环糊精手性固定相手性拆分性能的影响，本文采用点击化学制备了两种手性固定相：全取代-4-氯-3-甲基苯甲酰氨基-6A-三唑基-β-环糊精键合硅胶手性固定相（ CSP1）和全取代-5-氯-2-甲基苯甲酰氨基-6A-三唑基-β-环糊精键合硅胶手性固定相（ CSP2）。利用核磁共振、红外光谱及元素分析等手段对固定相的结构进行了表征；在反相高效液相色谱条件下，通过对9种黄烷酮消旋体的拆分，对比研究了两种固定相的手性拆分性能。研究结果表明 CSP1的拆分性能优于 CSP2。这两种手性固定相仅在水与甲醇体系下即可实现对黄烷酮的手性拆分，展现了较好的应用前景。

Cyclodextrin ( CD ) based chiral stationary phases ( CSPs ) have simulated great attention due to their unique chiral recognition ability. Functionalized cyclodextrins bonded sili-ca gel as chiral stationary phases have been dramatically developed due to their chemical stabil-ity and solvent tolerability. To explore the functionalization of phenylcarbamoylated β-cyclodex-trin CSPs on their enantioselectivities,4-chloro-3-methylaniline and 5-chloro-2-methyl phenyl isocyanate were employed. Two CSPs have been thus developed by clicking the CD derivatives onto alkynylated silica support. They include per-4-chloro-3-methylphenylcarbamoylated β-cyclodextrin clicked CSP( CSP1)and per-5-chloro-2-methylphenylcarbamoylated β-cyclodextrin clicked CSP( CSP2),which have both electron-donating( methyl)and withdrawing( chlorine) groups in the phenylcarbamate moieties,but different locations. The CSPs were successfully characterized in terms of structure using nuclear magnetic resonance( NMR ),Fourier trans-form infrared spectroscopy( FT-IR ) and elementary analysis. Their enantioselectivities were evaluated in reversed-phase high performance liquid chromatography( HPLC). The comparison study on the enantioseparation of nine flavonoids with the two CSPs demonstrates the higher enantioselectivities of CSP1 over CSP2,because of the different locations of electron-donating (methyl)and withdrawing(chlorine)groups in the phenylcarbamate moieties of CD deriva-tives. The baseline enantioseparations achieved in water/methanol as mobile phase offered great potential for the CSPs to be used in practical application.