Preparation And Chiral Recognition Ability Of Organic-inorganic Hybrid Materials Based On Polysaccharide Derivatives

Due to the high-efficiency and universal chiral separation capabilities,chiral stationary phases（CSPs）based on polysaccharide derivatives for high performance liquid chromatography（HPLC）have been widely used for enantioseparation.Up to now,the organic content of the polysaccharide chiral stationary phase prepared by coating and bonding methods is less than 20 wt%.Traditional coated chiral stationary phases cannot use some solvents with strong polarity as mobile phase components.This characteristic greatly limits the application of this type of chiral stationary phase in the field of chiral analysis and separation and preparative separation.Based on this background,this work prepared a series of amylose-based and microcrystalline cellulose-based organic-inorganic hybrid chiral stationary phases,and conduct an in-depth discussion on the chiral resolution properties and influencing factors of the prepared stationary phases.Amylose and microcrystalline cellulose tris（3,5-dimethylphenylcarbamate）derivatives containing 0%,2%and 4%of 3-（triethoxysilyl）propyl group were synthesized by carbamoylation method based on amylose and microcrystalline cellulose.Fourier Transform Infrared Spectrometer（FT-IR）and Proton Nuclear Magnetic Resonance（¹H NMR）were used to qualitatively and quantitatively characterize the structure of amylose derivatives.Finally,the obtained derivatives have regular structure and complete substitution.Then,a series of organic-inorganic hybrid materials based on the synthesized polysaccharide derivatives with high content of organic components are prepared by the alkali-catalyzed sol-gel method.The structure and morphology of the prepared hybrid materials were characterized and analyzed by FT-IR,²⁹Si NMR and SEM.Based on the prepared hybrid materials,the organic-inorganic hybrid chiral stationary phase was prepared by the homogenization method,and the chiral recognition performance was evaluated by high performance liquid chromatography,and the preparation conditions and organic component content were further explored.The characteristics of organic-inorganic hybrid materials and their influence on chiral recognition performance.The results indicated that the alkali-catalyzed sol-gel method proposed in this study can effectively prepare organic-inorganic hybrid microsphere materials with high content of organic components,and the morphology of the materials is regular and the content of organic components is controllable.In addition,the amount of reaction solvents such as alkali and water used in the preparation process and the content of organic components have a greater impact on the morphology,particle size distribution and chiral recognition performance of the hybrid material.When the amount of polysaccharide derivative is 0.25 g,the best ratio of TEOS/THF/H₂O/DEA for obtaining a structured hybrid material is 2/35/2/6.The organic-inorganic hybrid chiral fixation prepared in this article is relatively Tr（?）ger base（Rac-1）,2,3-diphenyl oxirane（Rac-2）,diphenylethanol ketone（Rac-3）,Flavanone（Rac-7）and binaphthol（Rac-9）have good chiral recognition performance,and the resolution performance of these chiral compounds exceeds that of the commonly used commercial column Chiralpak IA.