Polarity tuned perphenylcarbamoylated cyclodextrin separation materials for achiral and chiral differentiation

Publication date: 1 August 2018
Source:Talanta, Volume 185
Author(s): Xiaoxuan Li, Jia Li, Qing Kang, Yong Wang
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.

Graphical abstract

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