title: Chiral recognition of macromolecules with cyclodextrins: pH- and thermosensitive copolymers from N-isopropylacrylamide and N-acryloyl-D/L-phenylalanine and their inclusion complexes with cyclodextrins.
abstract: In the present work we report the enantioselective recognition of water soluble stimuli-responsive polymers bearing phenylalanine moieties via host-guest interaction with β-cyclodextrin and randomly-methylated-β-cyclodextrin (RAMEB-CD). We synthesised N-acryloyl-D/L-phenylalanine monomers (2(D), 2(L)) which were then copolymerised under free radical conditions with N-isopropylacrylamide (NIPAAm). The resulting copolymers 3(D) and 3(L) exhibit a lower critical solution temperature (LCST) of 25 °C. As a further benefit, the presence of a free carboxylic group in the copolymer system gives a high sensitivity to the pH value in respect to the LCST value. The enantioselective recognition of the side groups of copolymers 3(D) and 3(L) and their solubility behaviour were investigated by dynamic light scattering and 2D NMR spectroscopy, respectively.
authors: Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany.
authors: Sabrina
authors: S
authors: Gingter
authors: Ella
authors: E
authors: Bezdushna
authors: Helmut
authors: H
authors: Ritter