Molecular imprinting provides a means of creating tailor made molecular assemblies having structural and functional group complementarity to a template molecule. These molecularly imprinted polymers (MIPs) often have a high and selective affinity for the template over structurally related compounds. MIPs may therefore offer advantages over existing methods in chemical analysis. They are cheap and relatively facile to produce, and are stable, being able to withstand elevated temperatures and pressures. Applications of imprinting demonstrated so far include separation methods such as liquid chromatography (LC), immunoassay-type binding assays, and chemical sensors. Novel non-covalent monomer-template assemblies have been developed in an attempt to demonstrate an improvement in the recognition properties of MIPs. These assemblies draw on the thermodynamic principle that complexes between a template and chelating monomers should be entropically more favourable than complexes with monomers having just single points of interaction. More stable monomer-template assemblies, pre-polymerisation, should give rise to a larger proportion of high fidelity binding sites in the resulting polymer. In the first approach (Chapter 2) chelating dimers were developed, which have two acrylic acid groups joined by a benzene or biphenyl linker. The acrylic acid units were substituted in the ortho, meta and para positions on the benzene ring and in the para position on the biphenyl. Secondly, linear pre-polymers were synthesised, bearing carboxylic acid groups and grafted polymerisable acrylate side chains on their prepolymer backbone (Chapter 3). The dimers were used to imprint (-)-nicotine, and the linear pre-polymers were used to imprint (-)-nicotine and L-phenylalanine anilide (L-PAA). Recognition properties of the MIPs were assessed by using the polymers as chiral stationary phases (CSPs) in high performance liquid chromatography (HPLC). The linear pre-polymers and the ortho- and meta- substituted dimers were able to discriminate between a racemate ofthe template molecule. A novel method of imprinting cholesterol was developed whereby cholesterol was covalently bound to the monomer vinylbenzylamine through a sacrificial carbamate linker (Chapter 4). The carbamate was cleaved post polymerisation to leave primary amine groups located solely in cholesterol-selective binding sites.. These amine groups· were able to rebind cholesterol through non-eovalent interactions. Batch binding assays were used to assess the reco~tion properties of the imprinted and control polymers. Finally, a novel fluorescent monomer was synthesised and applied in the molecular imprinting of Boc-L-phenylalanine (Boc-L-Phe) (Chapter 5). Fluorescence of the imprinted polymer was seen to increase in the presence of the template, and this increase was greater for the imprinted polymer compared to the control polymer.