One-step fabrication of cinchona-based hybrid monolithic chiral stationary phases via photo-initiated thiol-ene polymerization for cLC enantioseparation

Although various click polymerization reactions (thiol-ene, thiol-yne, thiol-Michael, thiol-epoxy and amine-epoxy) have been utilized to prepare either hybrid or organic monolithic columns with homogeneous network structures, there were few reports on fabrication of monolithic CSPs via click polymer...

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Bibliographic Details
Published in:Talanta (Oxford) 2019-06, Vol.198, p.432-439
Main Authors: Ma, Shujuan, Wang, Yan, Zhang, Haiyang, Li, Ya, Ou, Junjie, Wei, Yinmao, Ye, Mingliang
Format: Article
Language:English
Subjects:
Capillary liquid chromatography
Chiral stationary phase
Hybrid monolith
Polyhedral oligomeric silsesquioxanes
Thiol-ene click reaction
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Summary:Although various click polymerization reactions (thiol-ene, thiol-yne, thiol-Michael, thiol-epoxy and amine-epoxy) have been utilized to prepare either hybrid or organic monolithic columns with homogeneous network structures, there were few reports on fabrication of monolithic CSPs via click polymerization. Herein, a fast and robust approach was explored to fabricate cinchona-based monolithic hybrid CSPs via photo-initiated thiol-ene polymerization within 10 min in one step. A self-synthesized octakis(3-mercaptopropyl) octasilsesquioxane (POSS-SH) was polymerized with phenylisocyanate cinchonidine (PCD) and (+)-N,N'-diallyl-L-tartardiamide (DATDA) or 1,2,4-trivinylcyclohexane (TVCH). The resulting two kinds of as-synthesized monolithic CSPs, poly(POSS-co-DATDA-co-PCD) and poly(POSS-co-TVCH-co-PCD), were evaluated for cLC enantioseparation of acidic racemates. It was found that they exhibited different enantioseparation ability due to using different multivinyl crosslinkers. The influence of ACN content in mobile phase on the enantioseparation of acidic racemates was investigated. The separation mechanism was also discussed on the basis of a comparison of enantioseparation on two kinds of hybrid monolithic CSPs. [Display omitted] •POSS-SH was self-synthesized to prepare hybrid monolithic chiral stationary phases.•Two kinds of monolithic CSPs were fabricated via photo-initiated thiol-ene polymerization within 10 min.•The kind of vinyl monomers affected enantioseparation ability in cLC.
ISSN:0039-9140
1873-3573
DOI:10.1016/j.talanta.2019.02.046