Influence of the linking spacer length and type on the enantioseparation ability of β-cyclodextrin functionalized monoliths

In order to investigate the effect of the linking spacer on the enantioseparation ability of beta-cyclodextrin (beta-CD) functionalized polymeric monoliths, three beta-CD-functionalized organic polymeric monoliths with different spacer lengths were prepared by using three amino-beta-CDs, i.e. mono-6-amino-6-deoxy-beta-CD, mono-6-ethylenediamine-6-deoxy-beta-CD, mono-6-hexamethylenediamine-6-deoxy-beta-CD, as starting materials. These amino-beta-CDs reacted with glycidyl methacrylate to produce functional monomers which were then copolymerized with ethylene dimethacrylate. The enantioseparation ability of the three monoliths was evaluated using 14 chiral acidic compounds, including mandelic acid derivatives, non steroidal anti-inflammatory drugs, N-derivatized amino acids, and chiral herbicides under optimum chromatographic conditions. Notably, the poly(GMA-NH2-beta-CD-co-EDMA) column provides higher enantioresolution and enantioselectivity than the poly(GMA-EDA-beta-CD-co-EDMA) and poly(GMA-HDA-beta-CD-co-EDMA) columns for most tested chiral analytes. Furthermore, the enantioseparation performance of triazole-linker containing monoliths was compared to that of ethylenediamine-linker containing monoliths. The results indicate that the enantioselectivity of beta-CD monolithic columns is strongly related to the length and type of spacer tethering beta-CD to the polymeric support. (C) 2016 Elsevier B.V. All rights reserved.