Boronic acid (BA) derivatives have been exploited for their strong and reversible interactions with diol-containing compounds for the recognition of saccharides, such as glucose. Combining BA groups and fluorescent moieties can allow for sugar concentrations to be monitored by changes in fluorescence. In this thesis, two approaches based on BA sensing capabilities are investigated. In a direct sensing approach, the BA group is covalently attached to the fluorescent reporter group. Conversely, in an indirect sensing approach, a two-component system is created when the BA group and fluorophore are incorporated in to separate molecules. A direct sensing approach is described in Chapter 2, where the BA derivatives employed contain a quinoline-5-carboxylic acid functionality. These BA fluorescent sensors were investigated for their glucose sensing capabilities in solutions of various pH and when immobilised on to a ‘lens-like’ platform. An indirect sensing approach is described in Chapter 3, where a BA-cationic pyrimidinium molecule, induced fluorescence quenching in an anionic fluorophore (7-hydroxycoumarin). On introducing glucose, the fluorescence was recovered. This sensing system was investigated in solutions of various pH. Chapter 4 details the synthesis of a new family of BA-monomers. These monomers were characterised by 11B NMR and fluorescence in the absence and presence of glucose. In Chapter 5, the BA-monomers described in Chapter 4 were investigated for indirect sensing with the anionic fluorophore pyranine in solution and in hydrogels. Finally, in Chapter 6, additional strategies for the integration of a two-component sensing in to hydrogel matrices are investigated. The aim of this research is the development of novel sensing systems that could be integrated in to a continuous glucose-monitoring device. Such a platform could offer diabetics personal control over monitoring their glucose levels, to aid the prevention of the side effects associated with the disease.