Surface-up construction of quinine bridged functional cyclodextrin for single-column versatile enantioseparation

Seeking for single-column versatile chiral separation methodology is the ultimate goal for analysts engrossed in enantioseparation. However, the versatility and selectivity are always contradictory due to negative influence among the recognition domains and the relatively low surface concentrations in a limited support surface area. Herein, we reported a novel series of quinine (QN) bridged cyclodextrin (CD) chiral stationary phases (CSPs) with satisfied surface concentration of both selectors, prepared via a facile surface-up 'thiol-ene click' approach, where QN and CD can not only nicely exhibit their individual resolution capability but also afford possible synergism in resolving difficult-to-separate analytes. QN bridged phenylcarbamoylated CD CSP exhibits powerful resolution ability by positive combining the resolving ability of QN and functional CD and achieves the resolution of almost a double number of racemates over QN or CD CSPs. Meanwhile, it exhibits comparable and even better chiral selectivity over the widely used chemical-bonded chiral column (CHIRALPAK® IA, CHIRALPAK® IB and CHIRALPAK® IC of Daicel) for the studied analytes. This work thus advances the duplex QN-CD structure as a relatively versatile platform for chiral resolution and commendably promotes the design of functional CSPs with chiral molecular bridge.