Study On Crown Ether Compounds As High Performance Liquid Chromatographic Chiral Stationary Phases

Chiral crown ethers as the chiral selectors have successfully been utilized in the separation of the enantiomers of α- amino acids with a good enantioselectivity. The four sections of the thesis are listed as follows:(1) R-(3,3’-diphenyl-1,1’-binaphthyl)-20-crown 6 was synthesized by(R)-1,1’– bi(2-naphthol). Compare to the reported literature, the synthetic route was changed by means of the suzuki reaction and its product yield was improved from 38% to 85%.(2) R-(3,3’-diphenyl-1,1’-binaphthyl)-20-crown 6 was coated on C18 silica gel and used as the chiral stationary phase of high performance liquid chromatography. We studied the chiral recognition ability for 13 kinds of α- amino acids enantiomer on the CSP, which 11 kinds of α-amino acid enantiomers were separated. The experimental results showed that the CSP possesses a good enantioselectivity for α-amino acid enantiomers.(3) Coated R-(3,3’-2-p-tolyl-1,1’-binaphthyl)-20-crown 6 on C18 silica gel as the chiral stationary phase of high performance liquid chromatography, 9 kinds of α-amino acid enantiomers were separated on the chiral colunm.(4) Bonding 3,3’-diphenyl-2,2’-dihydroxy-1,1’-binaphthyl to the silica gel via 3-aminopropyl-triethoxysilane, the column of high performance liquid chromatography was prepared. This column possessed good separations for positional isomers.