β-Cyclodextrin Functionalized Nanoporous Graphene Oxides for Efficient Resolution of Asparagine Enantiomers.

Abstract

Efficient resolution of racemic mixture has long been an attractive but challenging subject since Pasteur separated tartrate enantiomers in 19th century. Graphene oxide (GO) could be flexibly functionalized by using a variety of chiral host molecules and therefore, was expected to show excellent enantioselective resolution performance. However, this combination with efficient enantioselective resolution capability has been scarcely demonstrated. Here, nanoporous graphene oxides were produced and then covalently functionalized by using a chiral host material-β-cyclodextrin (β-CD). This chiral GO displayed enantioselective affinity toward the l-enantiomers of amino acids. In particular, >99 % of l-asparagine (Asn) was captured in a racemic solution of Asn while the adsorption of d-enantiomer was not observed. This remarkable resolution performance was subsequently modelled by using an attach-pull-release dynamic method. We expect this preliminary concept could be expanded to other chiral host molecules and be employed to current membrane separation technologies and finally show practical use for many other racemates.