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Insights into the origins of binding and the recognition properties of molecularly imprinted polymers prepared using an amide as the hydrogen‐bonding functional group
Author(s) -
Yu Cong,
Mosbach Klaus
Publication year - 1998
Publication title -
journal of molecular recognition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.401
H-Index - 79
eISSN - 1099-1352
pISSN - 0952-3499
DOI - 10.1002/(sici)1099-1352(199812)11:1/6<69::aid-jmr392>3.0.co;2-i
Subject(s) - molecularly imprinted polymer , hydrogen bond , methacrylic acid , chemistry , amide , molecular recognition , monomer , polymer , molecule , solvent , aqueous solution , selectivity , molecular imprinting , functional polymers , organic chemistry , polymer chemistry , combinatorial chemistry , copolymer , catalysis
Molecularly imprinted polymers (MIPs) prepared using an amide hydrogen‐bonding functional monomer (acrylamide) exhibited efficient enantiomeric recognition properties in both organic and aqueous media in the HPLC mode. The results indicate that the amide functional groups formed strong hydrogen‐bonding interactions with the template molecule, and specific recognition sites were created within the polymer matrix during the imprinting process. When Boc‐ L ‐Trp was used as the template, an MIP prepared in a polar organic solvent (acetonitrile) using acrylamide as the functional monomer showed better enantiomeric recognition of Boc‐Trp than the MIPs prepared in the same solvent using an acidic (methacrylic acid) or a basic (2‐vinylpyridine) functional monomer or a combination of an acidic and a basic functional monomer (methacrylic acid + 2‐vinylpyridine). Our results indicate that in organic media the degree of retention of the sample molecule on the imprinted polymer was controlled by hydrogen‐bonding interactions between the sample molecule and the polymer, while in aqueous media it was determined to a considerable extent by hydrophobic interactions. In both media the shape, size and the nature of the hydrogen‐bonding groups of the sample molecules were all important factors in determining the enantiomeric and substrate selectivity. In the aqueous media, however, the hydrophobicity of the sample molecules was also found to play an important role. Copyright © 1998 John Wiley & Sons, Ltd.