Synthesis of helical poly(phenylacetylene)s with amide linkage bearing L-phenylalanine and L-phenylglycine ethyl ester pendants and their applications as chiral stationary phases for HPLC
Synthesis of helical poly(phenylacetylene)s with amide linkage bearing L-phenylalanine and L-phenylglycine ethyl ester pendants and their applications as chiral stationary phases for HPLC
复制标题
带有 L-苯丙氨酸和 L-苯甘氨酸乙酯侧链的酰胺键螺旋聚苯乙炔的合成及其作为 HPLC 手性固定相的应用
DOI：
10.1021/ma4015802
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发表时间：
2013
期刊：
影响因子：
5.5
通讯作者：
Yoshio Okamoto
中科院分区：
文献类型：
--
作者：
Chunhong Zhang;Hailun Wang;Qianqian Geng;Taotao Yang;Lijia Liu;Ryosuke Sakai;Toshifumi Satoh;Toyoji Kakuchi;Yoshio Okamoto
合成了一种新型的带有L-苯丙氨酸和L-苯甘氨酸乙酯侧基的聚苯乙炔（PPA）手性固定相（PPA Phe和PPA Phg）。聚合物表现出不同的手性识别能力取决于涂层溶剂。PPA-Phe和PPA-Phg在CHCl 3包覆下均表现出较高的手性构象。它们的手性识别能力取决于分子量和旋光度，而分子量和旋光度又受聚合溶剂和单体浓度的影响，PPA-Phe和PPA-Phg表现出不同的手性，表明前者的苄基和后者的苯基在手性识别中也起重要作用。一些外消旋体在PPA-PheorPPA-Phg上完全分离，分离因子与流行的基于多糖的CSP上获得的分离因子相当或更高。
Novel stereoregular helical poly(phenylacetylene) derivatives (PPA-PheandPPA-Phg) with an amide linkage bearingl-phenylalanine andl-phenylglycine ethyl ester pendants were synthesized for use as chiral stationary phases (CSPs) in HPLC. The polymers showed different chiral recognition abilities depending on the coating solvents. BothPPA-PheandPPA-Phgexhibited higher chiral recognitions when coated with CHCl3by having preferable conformations. Their chiral recognition abilities depended on their molecular weight and optical rotations which were influenced by the polymerization solvents and monomer concentration.PPA-PheandPPA-Phgshowed rather different chiral recognitions, indicating that the benzyl group of the former and the phenyl group of the latter also play important roles in the chiral recognition. A few racemates were completely separated onPPA-PheorPPA-Phgwith separation factors comparable or higher than those obtained on the popular polysaccharide-based CSPs.