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
  • [31] Preparation of chiral stationary phases coated using cellulose derivatives and study of chiral resolution in HPLC
    Hou, JG
    Zhou, HY
    Jiang, SX
    Zhou, ZQ
    Chen, LR
    Ou, QY
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 1998, 19 (04): : 538 - 542
  • [32] Comparative studies of immobilized polysaccharide derivatives chiral stationary phases for enantioseparation of furanocoumarins and dihydroflavones and discussion on chiral recognition mechanism
    Tang, Luhuan
    Chen, Yanyan
    Wu, Mengru
    Tang, Tingting
    Yao, Yaqi
    JOURNAL OF SEPARATION SCIENCE, 2023, 46 (20)
  • [33] Novel cyclodextrin chiral stationary phases for high performance liquid chromatography enantioseparation: Effect of cyclodextrin type
    Lai, Xianghua
    Tang, Weihua
    Ng, Siu-Choon
    JOURNAL OF CHROMATOGRAPHY A, 2011, 1218 (33) : 5597 - 5601
  • [34] Comparison of enantioseparation of selected benzodiazepine and phenothiazine derivatives on chiral stationary phases based on β-cyclodextrin and macrocyclic antibiotics
    Tesarová, E
    Bosáková, Z
    JOURNAL OF SEPARATION SCIENCE, 2003, 26 (08): : 661 - 668
  • [35] Advanced dress-up chiral columns: New removable chiral stationary phases for enantioseparation of chiral carboxylic acids
    Todoroki, Kenichiro
    Ishii, Yasuhiro
    Ide, Takafumi
    Min, Jun Zhe
    Inoue, Koichi
    Huang, Xin
    Zhang, Wei
    Hamashima, Yoshitaka
    Toyo'oka, Toshimasa
    ANALYTICA CHIMICA ACTA, 2015, 882 : 101 - 111
  • [36] Enantioseparation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide and Macrocyclic Glycopeptide Chiral Stationary Phases
    Kazoka, Helena
    Turovska, Baiba
    Upmanis, Toms
    Veinberg, Grigory
    CHROMATOGRAPHIA, 2022, 85 (05) : 489 - 495
  • [37] Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases
    Dessi, Alessandro
    Sechi, Barbara
    Dallocchio, Roberto
    Chankvetadze, Bezhan
    Perez-Baeza, Mireia
    Cossu, Sergio
    Mamane, Victor
    Pale, Patrick
    Peluso, Paola
    CHIRALITY, 2022, 34 (04) : 609 - 619
  • [38] HPLC Enantioseparation of Novel Spirobrassinin Analogs on the Cyclofructan Chiral Stationary Phases
    Moskal'ova, Marianna
    Kozlov, Oleksandr
    Gondova, Tatana
    Budovska, Mariana
    Armstrong, Daniel W.
    CHROMATOGRAPHIA, 2017, 80 (01) : 53 - 62
  • [39] HPLC Enantioseparation of Novel Spirobrassinin Analogs on the Cyclofructan Chiral Stationary Phases
    Marianna Moskaľová
    Oleksandr Kozlov
    Taťána Gondová
    Mariana Budovská
    Daniel W. Armstrong
    Chromatographia, 2017, 80 : 53 - 62
  • [40] Optimization of Liquid Crystalline Mixtures Enantioseparation on Polysaccharide-Based Chiral Stationary Phases by Reversed-Phase Chiral Liquid Chromatography
    Urbanska, Magdalena
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (12)