Molecular imprinting technology is a field of analytical chemistry of ever-increasing importance, offenng an effective and economic means of producing molecule-specific synthetic materials, with potential application in separation, sensing and catalytic technologies. This thesis descnbes a detailed investigation of the method and examines how it may be incorporated into a typical analytical application (solid phase extraction of the active ingredient in a pharmaceutical preparation), and investigates some of the practical considerations of such an approach - choice of appropriate functional monomer, the possibility of swelling effects affecting recognition properties of the polymers, and the use of pH control to adjust selectivity when recognition is based on ionic interactons. The performance of the MIPs presented in the second chapter is then used as a platform for probing more fundamental aspects of MIP behaviour. Properties of pre-polymerisaton mixtures which have consequences for final MIP recognition behaviour are examined in detail in Chapters three and four, with NMR spectroscopy (coupled with subsequent HPLC evaluation of the MIP recognition capabilities) playing an important role. The impact of more subtle effects, such as n-n stacking and phase partition, is of particular note Chapter five shows how spectroscopic data, as acquired in Chapter 4, can be used to refine simulated models of pre-polymerisaton complexes, which may be of significant benefit in predicting MIP properties and ultimately in creating a step-by-step protocol for designing efficient MIPs.