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Thiol‐ene click derived structurally well‐defined per(3,5‐dimethyl)phenylcarbamoylated cationic cyclodextrin separation material for achiral and chiral chromatography
Author(s) -
Tang Xiaoying,
Li Xiaoxuan,
Sun Yuwei,
Xiao Yin,
Wang Yong
Publication year - 2018
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201800207
Subject(s) - chemistry , cationic polymerization , cyclodextrin , ene reaction , benzene , high performance liquid chromatography , fourier transform infrared spectroscopy , thiol , click chemistry , chiral resolution , xylene , resolution (logic) , organic chemistry , covalent bond , proton nmr , chromatography , enantiomer , chemical engineering , artificial intelligence , computer science , engineering
In this work, a novel single sulfoether‐bridged cationic per(3,5‐dimethyl)phenylcarbamoylated‐β‐cyclodextrin separation material was prepared by thiol‐ene click chemistry and characterized by using FTIR spectroscopy, solid‐state 13 C NMR spectroscopy and elemental analysis, which confirmed the correct structure. The separation material exhibited a good achiral separation performance for benzene homologues and phenylamine analogs, especially o ‐xylene and m ‐xylene, and m ‐phenylenediamine and o ‐phenylenediamine can be discriminated by the (3,5‐dimethyl)phenylcarbamoyl cyclodextrins. The chiral resolving ability of the separation material was evaluated by discriminating various isoxazolines, flavonoids, and β‐blockers in reversed‐phase high‐performance liquid chromatography. For isoxazolines, the material showed the best chiral discrimination toward 3‐aryl‐5‐(2‐oxopyrrolidin‐1‐yl)‐isoxazolines, where the resolution for 3ClPh‐OPr reached 6.03. For flavonoids, it exhibited more efficient separation to the ones with more hydrophobic substituents, with a resolution of 5.93 for 6‐hydroxyflavanone. β‐Blockers were also enantioseparated satisfactorily on the material. The as‐prepared separation material is a good member of the thiol‐ene click derived cyclodextrin stationary phase family.