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Published on: August 15, 2018
Polarity tuned perphenylcarbamoylated cyclodextrin separation materials for achiral and chiral differentiation
Xiaoxuan Li1, Jia Li1, Qing Kang1
1Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
Abstract:
Phenylcarbamoyls are known to remarkably accentuate cyclodextrin's enantioselectivities. In this work, by inducing electron-donating methoxyl or electron-withdrawing bromine/trifluoromethyl moieties, three novel cyclodextrin enantioseparation materials including per(4-trifluoromethoxy) phenylcarbamoylated-β-CD CSP (CSP1), per(4-bromo)phenylcarbamoylated-β-CD CSP (CSP2) and per(4-methoxy)phenylcarbamoylated-β-CD CSP (CSP3) were prepared via thiol-ene click chemistry. The polarity tuning decorations are found to significantly influence the CSPs' achiral and chiral separation performance. The three CSPs can easily separate toluene, 1,2-xylene and 1,3,5-trimethylbenzene with the strongest retention on CSP3. In reversed-phase mode, the three CSPs exhibited completely different enantioseparation ability towards specific isoxazolines and flavonoids. 4'-hydroxyflavanone was separated on CSP1 with a resolution of 9.24 while 6-methoxyflavanone was best separated on CSP2 (Rs = 9.98). CSP3 exhibited the strongest differentiation ability towards 4NPh-2Py (Rs = 9.69). The comparison study may provide some insight into the design of functional cyclodextrin materials.
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