Preparation of a 1,1'-Binaphthyl-based Chiral Polyimine Macrocycle Bonded Chiral Stationary Phase by Thiol-ene Click Reaction and Its Enantioseparation Performance in High-Performance Liquid Chromatography

被引:1
作者
Wu, Jia-Lei [1 ]
Yu, Li-Qin [1 ]
Zhang, Hua-Can [1 ]
Wang, Bang-Jin [1 ]
Xie, Sheng-Ming [1 ]
Zhang, Jun-Hui [1 ]
Yuan, Li-Ming [1 ]
机构
[1] Yunnan Normal Univ, Coll Chem & Chem Engn, Kunming, Peoples R China
基金
中国国家自然科学基金;
关键词
chiral polyimine macrocycle; chiral stationary phase; enantioseparation; high-performance liquid chromatography; thiol-ene click reaction; BETA-CYCLODEXTRIN; CHEMISTRY; SEPARATION; DERIVATIVES; RESOLUTION; COMPLEXES; SELECTORS; BINOL;
D O I
10.1002/jssc.70064
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Chiral macrocycles have emerged as attractive media for chromatographic enantioseparation due to their excellent host-guest recognition properties. In this study, a new chiral stationary phase (CSP) based on 1,1'-binaphthyl chiral polyimine macrocycle (CPM) was reported. The CPM was synthesized by one-step aldehyde-amine condensation of (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde with 1,2-phenylenediamine and bonded on thiolated silica via the thiol-ene click reaction to afford the CSP. The enantioseparation performance of the CSP was evaluated by separating different types of racemates including alcohols, esters, ketones, amides, organic acids, and ethers in both normal-phase (NP) and reversed-phase (RP) elution modes. As a result, enantioseparations of 10 and 15 racemates were achieved in the two elution modes, respectively. Meanwhile, the effects of chromatographic conditions on separation, such as mobile phase composition and injection mass, were studied in detail. Moreover, a comparison of the proposed CSP for the separation of the tested racemates with commercial Chiralcel OD-H and Chiralpak AD-H columns was also conducted, and results revealed that the proposed CSP can achieve some enantioseparations that cannot be achieved by the two commercial columns. This study indicates that the chiral macrocycle is a promising chiral selector for high-performance liquid chromatography.
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页数:11
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共 60 条
[1]   Chiral analysis in food science [J].
Alvarez-Rivera, Gerardo ;
Bueno, Monica ;
Ballesteros-Vivas, Diego ;
Cifuentes, Alejandro .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2020, 123
[2]   SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES [J].
ARMSTRONG, DW ;
WARD, TJ ;
ARMSTRONG, RD ;
BEESLEY, TE .
SCIENCE, 1986, 232 (4754) :1132-1135
[3]   MACROCYCLIC ANTIBIOTICS AS A NEW CLASS OF CHIRAL SELECTORS FOR LIQUID-CHROMATOGRAPHY [J].
ARMSTRONG, DW ;
TANG, YB ;
CHEN, SS ;
ZHOU, YW ;
BAGWILL, C ;
CHEN, JR .
ANALYTICAL CHEMISTRY, 1994, 66 (09) :1473-1484
[4]   Application of cellulose 3,5-dichlorophenylcarbamate covalently immobilized on superficially porous silica for the separation of enantiomers in high-performance liquid chromatography [J].
Bezhitashvili, Lia ;
Bardavelidze, Anna ;
Mskhiladze, Antonina ;
Gumustas, Mehmet ;
Ozkan, Sibel A. ;
Volonterio, Alessandro ;
Farkas, Tivadar ;
Chankvetadze, Bezhan .
JOURNAL OF CHROMATOGRAPHY A, 2018, 1571 :132-139
[5]   Effect of pore-size optimization on the performance of polysaccharide-based superficially porous chiral stationary phases for the separation of enantiomers in high-performance liquid chromatography [J].
Bezhitashvili, Lia ;
Bardavelidze, Anna ;
Ordjonikidze, Teona ;
Chankvetadze, Lali ;
Chity, Mike ;
Farkas, Tivadar ;
Chankvetadze, Bezhan .
JOURNAL OF CHROMATOGRAPHY A, 2017, 1482 :32-38
[6]   Amino acids, peptides, and proteins as chemically bonded stationary phases - A review [J].
Bocian, Szymon ;
Skoczylas, Magdalena ;
Buszewski, Boguslaw .
JOURNAL OF SEPARATION SCIENCE, 2016, 39 (01) :83-92
[7]   BINOL: A versatile chiral reagent [J].
Brunel, JM .
CHEMICAL REVIEWS, 2005, 105 (03) :857-897
[8]   Application of click chemistry on preparation of separation materials for liquid chromatography [J].
Chu, Changhu ;
Liu, Renhua .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2177-2188
[9]   Chiral self-sorting and guest recognition of porous aromatic cages [J].
Cui, Dong-Xu ;
Geng, Yun ;
Kou, Jun-Ning ;
Shan, Guo-Gang ;
Sun, Chun-Yi ;
Zhang, Kun-Hao ;
Wang, Xin-Long ;
Su, Zhong-Min .
NATURE COMMUNICATIONS, 2022, 13 (01)
[10]   Thiol-yne Click Post-Modification for the Synthesis of Chiral Microporous Organic Networks for Chiral Gas Chromatography [J].
Cui, Yuan-Yuan ;
Yang, Cheng-Xiong ;
Yan, Xiu-Ping .
ACS APPLIED MATERIALS & INTERFACES, 2020, 12 (04) :4954-4961