以分子印迹聚合物为固定相手性拆分1,1′-联-2-萘酚及其衍生物  

Resolution of Racemic 1,1′-Bi-2-Naphthol and Its Derivatives by Molecularly Imprinted Polymers

作　　者：李丽虹[1] 刘岚[1] 罗勇[1] 邓芹英[1] 

机构地区：[1]中山大学化学与化学工程学院,广东广州510275

出　　处：《色谱》2006年第6期574-577,共4页Chinese Journal of Chromatography

基　　金：国家自然科学基金资助项目(No.20202015);教育部博士点基金(No.20020558026)

摘　　要：以(R)-(+)-1,1′-联-2-萘酚为模板分子,4-乙烯基吡啶为功能单体合成了分子印迹聚合物,将其作为高效液相色谱的固定相,研究其手性识别特性。对该固定相的手性拆分的色谱条件进行了优化。实验结果表明,合成的印迹聚合物对(R)-(+)-1,1′-联-2-萘酚具有较强的亲和力和特定的选择性,能有效拆分1,1′-联-2-萘酚对映体,分离因子最高达到12.25。通过优化色谱条件,该分子印迹聚合物还能对与1,1′-联-2-萘酚结构相似的衍生物5,6,7,8,5′,6′,7′,8′-八氢-1,1′-联-2-萘酚和1,1′-联萘-2-氨基-2′-酚进行手性拆分,分离因子分别达到1.51和2.40。1,1 ′-Bi-2-naphthol is one of the most popular analytes in chiral separation since optically active 1, 1 ′-bi-2-naphthol and its derivatives are frequently used as chiral auxiliaries and ligands in asymmetric synthesis. Therefore, it was employed as template for the preparation of molecularly imprinted polymer （MIP） which was used as liquid chromatographic stationary phase. In this study, the MIP was prepared by bulk polymerization using （R）-（ ＋ ）-1, 1′-bi-2- naphthol as template molecule, 4-vinyl pyridine, ethylene glycol dimethacrylate and acetonitrile as functional monomer, cross-linker and porogen respectively. High performance liquid chromatography （HPLC） was employed to study the chiral recognition properties of the resulting MIP. The effect of chromatographic conditions, such as the composition of mobile phase, flow rate and column temperature, on the enantioseparation were systematically investigated. It was experimentally shown that the MIP had specific interactions and high affinity with the template molecule. The MIP could effectively resolve the rac-1, 1 ′-bi-2-naphthol, and the separation factor was found to be 12.25 under the following conditions： mobile phase, acetonitrile-acetic acid （99： 1, v/v） ; flow rate, 1.2 mL/min; column temperature, 30 ℃. The addition of acetic acid to the mobile phase can improve the peak shape, and the lower flow rate and lower column temperature is better for the separation. Further, other substrates which have the similar structure with 1,1 ′-bi-2-naphthol , i. e, 5,6,7,8,5′, 6′, 7′, 8 ′-octahydro- 1,1 ′-bi-2-naphthol and 1, 1 ′- binaphthalenyl-2-amino-2′-ol were also resolved partly by optimizing the HPLC conditions, with separation factors of 1. 51 and 2.40, respectively.

关 键 词：分子印迹聚合物 高效液相色谱 联萘酚 手性拆分 

分 类 号：O658[理学—分析化学]