Recent advances in helical polyacetylene derivatives used as coated chiral stationary phases for enantioseparation

被引:21
作者
Wu, Guanzhao [1 ]
机构
[1] Shandong Univ, Qilu Hosp Qingdao, Dept Cent Lab & Mitochondrial Med Lab, Cheeloo Coll Med, Qingdao, Peoples R China
关键词
ETHYL-ESTER PENDANTS; BEARING; RECOGNITION; POLY(PHENYLACETYLENE)S; POLYMERIZATION; SEPARATION; POLYMERS; MEMORY; HPLC;
D O I
10.1039/d2py00366j
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Chiral separation by high-performance liquid chromatography (HPLC) using a chiral stationary phase (CSP) is a reliable method for obtaining pure enantiomers for both analytical and preparative purposes. The development of effective CSPs is the key point of this technique. Among many synthetic polymers showing chiral recognition abilities, the helical polyacetylene derivatives with stereoregular structures showed excellent chiral recognition abilities as CSPs and are promising candidates as CSPs for HPLC. Dynamic helical polyacetylene derivatives can change their helical pitch and invert the helicity by changing their functional chiral pendants. The change of helical conformation will significantly influence their chiral recognition abilities. In this review, the development of helical polyacetylene derivatives bearing different kinds of chiral pendants (central chirality pendants, axial chirality pendants, planar chirality pendants, and helical chirality pendants) and the enantioseparation based on these helical polymers as coated CSPs for HPLC will be described. The chiral recognition potential of helical polyacetylene derivatives bearing spiro and multilayer 3D chirality pendants is discussed for future study. We hope this review will inspire more motivation to develop novel helical polyacetylene derivatives showing highly efficient chiral recognition and resolution ability for a wide range of racemates.
引用
收藏
页码:3036 / 3047
页数:12
相关论文
共 50 条
  • [1] Effect of pendant stereostructure on backbone conformation and enantioseparation ability of helical polyacetylene-based chiral stationary phases
    Shi, Ge
    Li, Yue
    Dai, Xiao
    Shen, Jun
    Wan, Xinhua
    CHIRALITY, 2022, 34 (04) : 574 - 586
  • [2] Synthesis and enantioseparation of proline-derived helical polyacetylenes as chiral stationary phases for HPLC
    Shi, Ge
    Dai, Xiao
    Zhou, Yue
    Zhang, Jie
    Shen, Jun
    Wan, Xinhua
    POLYMER CHEMISTRY, 2020, 11 (18) : 3179 - 3187
  • [3] Effect of Substituent on the Enantioseparation Property of Helical Polyacetylene-based Chiral Stationary Phases for High-performance Liquid Chromatography
    Li, Yue
    Shi, Ge
    Kang, Shu-ming
    Zeng, Hua
    Zhang, Jie
    Wan, Xin-hua
    ACTA POLYMERICA SINICA, 2023, 54 (05): : 612 - 621
  • [4] Enantioseparation characteristics of chiral stationary phases based on the derivatives of cellulose and chitin
    Wang, Xiao-Chen
    Zhang, Juan
    Xu, Xiao-Qin
    Chen, Wei
    Yang, Yong-Gang
    Bai, Zheng-Wu
    ANALYTICAL METHODS, 2015, 7 (06) : 2786 - 2793
  • [5] Recent advances of optically active helical polymers as adsorbents and chiral stationary phases for chiral resolution
    Yuan, Shuyi
    Zhao, Lei
    Wang, Fangqin
    Tan, Lilan
    Wu, Datong
    JOURNAL OF SEPARATION SCIENCE, 2023, 46 (18)
  • [6] Synthesis of Proline-Derived Helical Copolyacetylenes as Chiral Stationary Phases for HPLC Enantioseparation
    Li, Yue
    Kang, Shu-Ming
    Shi, Ge
    Chen, Yi-Fu
    Li, Bo-Wen
    Zhang, Jie
    Wan, Xin-Hua
    CHINESE JOURNAL OF POLYMER SCIENCE, 2025, 43 (01) : 61 - 69
  • [7] Enantioseparation using helical polyacetylene derivatives
    Zhang, Chunhong
    Liu, Lijia
    Okamoto, Yoshio
    TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2020, 123
  • [8] Chromatographic enantioseparation of chiral sulfinamide derivatives on polysaccharide-based chiral stationary phases
    Zeng, Qingle
    Wen, Quan
    Xiang, Yao
    Zhang, Lei
    JOURNAL OF CHROMATOGRAPHY A, 2018, 1571 : 240 - 244
  • [9] Enantioseparation on Helical Poly(phenylacetylene)s Bearing Cinchona Alkaloid Pendants as Chiral Stationary Phases for HPLC
    Naito, Yuki
    Tang, Zhenglin
    Iida, Hiroki
    Miyabe, Toshitaka
    Yashima, Eiji
    CHEMISTRY LETTERS, 2012, 41 (08) : 809 - 811
  • [10] Synthesis and Enantioseparation Ability of Xylan Bisphenylcarbamate Derivatives as Chiral Stationary Phases in HPLC
    Li, Geng
    Shen, Jun
    Li, Qiang
    Okamoto, Yoshio
    CHIRALITY, 2015, 27 (08) : 518 - 522