Preparation And Chiral Recognition Of Chiral Stationary Phases Based On Cellulose And Amylose Derivatives

High performance liquid chromatography (HPLC) is one of the effective means for chiral separation. It can be used for not only analytical but also preparative separation. Developing chiral stationary phases (CSPs) is one of the great concerns in the field of chiral separation. CSPs based on polysaccharide derivatives, such as cellulose and amylose, show high chiral recognition ability. In this thesis,12 novel polysaccharide derivatives-based CSPs were developed for HPLC enantioseparation.A series of 9 novel coated-type chiral stationary phases based on polysaccharide derivatives were prepared. The obtained derivatives were characterized by infrared spectrum (IR),1HNMR spectrum, and elemental analysis and their performances were evaluated by eight pairs of racemates. It was revealed that the nature and location of the substituent had a significant impact on chiral recognition. Compared to the widely-used, commercially available columns, Chiralpak AD and Chiralcel OD, the prepared CSPs exhibited lower chiral recognition.With less 2-propanol added in the mobile phases, better resolutions were obtained. Additionally, when ethanol was used as mobile phase additive instead of 2-propanol, poorer enantioseparations were achieved.Three novel regioselectively substituted amylose derivatives with three different substituents at the 2-,3-, and 6- positions of the glucose unit were prepared. They were characterized by IR,]H NMR spectrum, and elemental analysis and their performances were evaluated. It was found that the obtained derivatives demonstrated characteristic enantioseparation. The chiral recognition abilities of the obtained CSPs were increased with the decrease of the mobile phase s polarity and affected by the nature and location of the substituents. Compared with Chiralpak AD, the obtained amylose derivatives showed comparable or higher chiral recognition ability for some racemates. Among the derivatives, amylose 2-benzoyl-3-(5-chloro-2-methylphenylcarbamate)-6-(3,5-dichlorophenylca-rbamate) demonstrated the best enantioseparatins for the tested racemates and its chiral recogntion was comparable to Chiralpak AD.