Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (12): 1355-1361.DOI: 10.6023/A1202023 Previous Articles     Next Articles

Special Topic


王怀松a,b, 彭江涛b,c, 魏纪平b, 姜安b,c   

  1. a 南京大学化学化工学院 南京 210093;
    b 江苏省质量安全工程研究院 南京 210046;
    c 南京财经大学管理科学与工程学院 南京 210046
  • 投稿日期:2012-02-23 修回日期:2012-04-23 发布日期:2012-04-20
  • 通讯作者: 姜安

Synthesis of Novel Chiral Stationary Phase Based on Atom Transfer Radical Polymerization and Click Chemistry

Wang Huaisonga,b, Peng Jiangtaob,c, Wei Jipingb, Jiang Anb,c   

  1. a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093;
    b Jiangsu Province Institute of Quality & Safety Engineering, Nanjing 210046;
    c School of Management Science & Industrial Engineering, Nanjing University of Finance & Economics, Nanjing 210046
  • Received:2012-02-23 Revised:2012-04-23 Published:2012-04-20

A novel chiral stationary phase was synthesized via the combination of atom transfer radical polymerization (ATRP) and click chemistry. In the synthesis, the silane coupling agent 3-(2-bromoisobutyryl)- propyl triethoxysilane (BPE) was chosen as the ATRP initiator and immobized on the porous silica gel. The polymer chains of poly(2-methyl-3-butyn-2-ol methacrylate) (pMBMA) were grafted on the silica substrates by surface-initiated ATRP. This “grafting-from” technique was used to synthesize polymers with controllable molecular weight and narrow molecular weight distributions. For immobilizing the chiral selector, azide-modified β-cyclodextrin (β-CD) was synthesized and bounded on the pMBMA by click chemistry, which can avoid the side-reactions in the preparation. The materials with different pMBMA chain density and length on the silica gel surface were prepared. Several pharmaceuticals were used to evaluate the enantioseparation ability of the materials under reversed-phase high performance liquid chromatography. The results demonstrate that ATRP can well design the polymer structure, and click chemistry can provide an effective route in the β-CD immobilization for chiral discrimination. It was found that the retention and separation factors of chiral compounds could be improved by adjusting the pMBMA chain density and length on the surface of silica gel.

Key words: chiral stationary phase, atom transfer radical polymerization (ATRP), β-cyclodextrin (β-CD), click chemistry