Chiral recognition of enantiomeric isobornyl methacrylate‐containing hydrogels with α‐cyclodextrin

Abstract

Two enantiomers of isobornyl methacrylate (iBMA) were prepared by reducing (1R,4R)‐(+)‐camphor and (1S,4S)‐(−)‐camphor followed by simple methacrylation reaction. The iBMA enantiomers were incorporated into hydrophilic polymer networks by free radical polymerization with N,N‐dimethylacrylamide and diethylene glycol dimethacrylate at different molar ratios. The influence of α‐cyclodextrin (α‐CD) and randomly methylated β‐cyclodextrin (rβ‐CD), and thereby enantioselectivity, on the swelling behaviour of the enantiomeric networks in water and alcoholic solutions was examined. An increase of swelling was observed on addition of α‐CD and rβ‐CD. While rβ‐CD showed a greater influence on the swelling itself, only α‐CD was able to achieve a minor differentiation between the polymer networks by their enantiomeric components and therefore a chiral recognition of the iBMA moieties. These results were validated using rheological measurements. © 2015 Society of Chemical Industry