title: Preparation and application of abietic acid-derived optically active helical polymers and their chiral hydrogels.
abstract: A novel chiral monomer N-propargyl abietamide, M1, was synthesized from abietic acid and catalytically polymerized with (nbd)Rh+B-(C6H5)4 (nbd=norbornadiene), providing polymer [poly(1)] with a molecular weight of 13,000-36,000 at a yield of 59-84%. Poly(1) did not form stable helices in tetrahydrofuran at room temperature whereas copolymerization of M1 and the achiral N-propargylamide monomer, M2, led to the formation of helical optically active copolymers as indicated by circular dichroism studies, UV-vis spectroscopy, and specific optical rotation measurements. Hydrogels were prepared based on an optically active helical copolymer, poly(M1(0.32)-co-M2(0.68)) that exhibited enantioselective recognition toward l-alanine. The novel chiral polymers derived from abietic acid are expected to find applications in such areas as chiral recognition, chiral resolution, and chiral catalysis.
authors.affiliation: State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China.
authors.forename: Fei
authors.initials: F
authors.lastname: Yao
authors.forename: Dongyue
authors.initials: D
authors.lastname: Zhang
authors.forename: Chaohong
authors.initials: C
authors.lastname: Zhang
authors.forename: Wantai
authors.initials: W
authors.lastname: Yang
authors.forename: Jianping
authors.initials: J
authors.lastname: Deng
mesh_terms: D045784:Abietanes / Q000138:chemical synthesis*; D000409:Alanine / Q000737:chemistry*; D020100:Hydrogels / Q000138:chemical synthesis*; D008968:Molecular Conformation; D008970:Molecular Weight; D011108:Polymers / Q000737:chemistry*
chemical_list: D045784:Abietanes; D020100:Hydrogels; D011108:Polymers; D000409:Alanine; C023710:abietic acid