Abstract
The nature of molecular recognition in an imprinted polymer that is formed by the self-assembly of binding monomer and imprint through noncovalent interactions is investigated. The system studied uses ethylene glycol dimethacrylate, methacrylic acid, and l-phenylalanine anilide as the cross-linking monomer, binding monomer, and imprint, respectively, to assemble the imprinted polymer. A proposal for the self-assembly mechanism between the binding monomer and imprint that occurs during polymer synthesis is derived from a single-crystal X-ray structure of a crystal containing binding monomer and imprint and from 1H NMR and FTIR spectroscopy of solutions of these components. These studies show the presence of a salt-bridge interaction that leads to a 1:1 molecular complex between methacrylic acid and l-phenylalanine anilide and provide no evidence for the formation of higher-order molecular complexes of these species. Furthermore, macroscopic phase separation is observed between the imprint and binding monom...
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