Date of Award

1-1-2011

Document Type

Campus Access Thesis

Department

Chemistry and Biochemistry

Sub-Department

Chemistry

First Advisor

Ken D Shimizu

Abstract

Presented is the development of a new strategy for enhancing the utility and efficiency of the molecular imprinting process. Our strategy is to design a multi-functional monomer that can form intramolecular hydrogen bonds. The purpose of this design is to significantly reduce the number of unwanted background sites in the polymer matrix, which limits the selectivity and overall binding affinity of molecular imprinting polymers.

Imprinted and non-imprinted polymers formed using the new multi-functional monomers showed low numbers of background sites as predicted. However, the reduction in the number of background sites was due to the formation of both intra and intermolecular hydrogen bonding within the monomer. Both types of hydrogen bonding contributed effectively in suppressing the numbers of background binding sites in the polymer matrix.

Another aspect of our work examined the influence of the solvent system used in the polymerization mixture on the imprinting effect. The goal of this work was to specifically study how solvents with different polarities and hydrogen bonding abilities can affect the imprinting process, and whether a reasonable predictive model can be generated.

Six different polar additives were added in varying percentages to the polymerization solution. The polar solvents systematically disrupted the imprinting effect as seen by the lower binding capacities of the imprinted polymers formed with higher mole fraction of polar solvent. Results showed a linear correlation between the hydrogen bonding abilities of the solvents and the degree of disruption of templation and dimerization in the polymer matrix. Results also showed that it requires a very high percentage of polar solvent to completely disrupt the imprinting and monomer aggregation effects.

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