Synthesis of optically active macroporous poly( N-isopropylacrylamide) hydrogels with helical poly( N-propargylamide) for chiral recognition of amino acids

• Published in: Reactive & functional polymers Vol. 71; no. 9; pp. 972 - 979
• Main Authors: Li, Lei, Du, Xiaoying, Deng, Jianping, Yang, Wantai
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier B.V 01.09.2011; Elsevier
• Subjects: Amino acids; Applied sciences; Architecture; Chiral recognition; Copolymerization; Crosslinking; Exact sciences and technology; Free radicals; Helical; Helical copolymer; Hydrogels; Macroporous structure; Optical activity; Optically active hydrogels; Organic polymers; Physicochemistry of polymers; Polyethylene glycol; Preparation, kinetics, thermodynamics, mechanism and catalysts; Amino acids; Macroporous structure; Chiral recognition; Helical copolymer; Optically active hydrogels; Terpolymerization; Graft copolymer; Enantioselectivity; Acrylamide derivative copolymer; Chiral compound; Porous material; Colloidal gel; Swelling; Phenylalanine; Liquid solid adsorption; Selective adsorption; Tryptophan; Acetylene derivative copolymer; Experimental study; Complex catalyst copolymerization; Optically active copolymer; Conjugated copolymer; Aminoacid; Morphology; Preparation; Carboxamide; Prepolymer; Kinetics; Radical copolymerization; Macroporosity
• ISSN: 1381-5148
• DOI: 10.1016/j.reactfunctpolym.2011.06.006

Optically active macroporous poly( N-isopropylacrylamide) (PNIPAM) hydrogels were synthesized via free radical copolymerization of NIPAM, helical macromonomer, and cross-linker N, N′-methylenebisacrylamide. The helical macromonomer not only contained catechol groups but also vinyl groups in side chains. Polyethylene glycols were used as pore-forming agent to give rise to macroporous structures in the optically active hydrogels. The hydrogels were characterized by FT-IR, SEM, DSC, swelling ratio and circular dichroism spectra analyses and exhibited the expected optical activity and macroporous architectures. The chiral resolution tests demonstrated the preferential adsorption of the hydrogels towards d-tryptophan and d-phenylalanine in the corresponding two amino acid enantiomers.