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采用Rh(nbd)BPh4催化剂合成了3种侧链带有L-氨基酸乙酯的螺旋聚苯乙炔衍生物PPA-S-Phe、PPA-S-Leu和PPA-A-Leu,并将其涂覆在氨丙基硅胶上制备高效液相色谱(HPLC)手性固定相(CSP),研究其对7种对映体的手性识别能力.由于侧链手性基团或主链与手性基团之间的链接基团不同,PPA-S-Phe、PPA-S-Leu和PPA-A-Leu形成了不同的螺旋构象,并表现出对对映体不同的手性识别能力.PPA-S-Phe和PPA-S-Leu的主链与手性基团之间的链接基团均为磺酰胺基,侧链手性基团为L-亮氨酸乙酯的PPA-S-Leu的手性识别能力优于侧链手性基团为L-苯丙氨酸乙酯的PPA-S-Phe.PPA-S-Leu和PPA-A-Leu的侧链手性基团均为L-亮氨酸乙酯,以酰胺基为链接基团的PPA-A-Leu的手性识别能力明显优于以磺酰胺基为链接基团的PPA-S-Leu.螺旋聚苯乙炔主链与侧链手性基团之间的链接基团、侧链手性基团在手性识别中均发挥十分着重要作用.
Three kinds of PSAs PPA-S-Phe, PPA-S-Leu and PPA-A-Leu with side-chain L-amino acid ethyl ester were synthesized by Rh (nbd) BPh4 catalyst, High performance liquid chromatography (HPLC) chiral stationary phase (CSP) was prepared on aminopropyl silica gel and its chiral recognition ability on seven enantiomers was studied.As the side chain chirality or backbone and chirality PPA-S-Phe, PPA-S-Leu and PPA-A-Leu form different helical conformations and show different chiral recognition ability for enantiomers.PPA-S Phe and PPA-S-Leu in which the linking group between the main chain and the chiral group is a sulfonamide group and the side chain chiral group is L-leucine ethyl ester, PPA-S-Leu The ability of recognition is better than that of PPA-S-Phe, whose side chain chirality is L-phenylalanine ethyl ester.The side chain chirality groups of PPA-S-Leu and PPA-A-Leu are all L-light The chiral recognition ability of PPA-A-Leu with amide group as the linking group is obviously better than that of PPA-S-Leu with the sulfonamide group as the linking group. Chiral groups between the link groups, side chain chiral groups in chiral recognition play a very important role.