Redox active molecules with molecular electronics and synthetic applications

Redox active molecules are ubiquitous to nature and have properties that make them coveted targets for applications in areas of synthesis as well as for the development of materials. This thesis describes the synthesis and characterisation of several flavin donor-acceptor dyads designed around an oligothiophene donor backbone and a flavin acceptor moiety. These show potential applications as optoelectronic materials. It also describes the synthesis of a ferrocene-flavin tetracyanobutadiene super-acceptor compound which showed preliminary evidence of non-linear-optic effects. Finally, a novel method was developed to investigate the redox umpolung activated reactions of vinylferrocene. The vinyl group of vinylferrocene was activated by polarity inversion of ferrocene to ferrocenium and was able to undergo Diels-Alder cycloadditions with cyclobutadiene and furan, as well as, Markovnikov addition of thiols. These reactions were then used to explore the use of vinylferrocene as a redox auxiliary and as a redox active tag in polymers and have the potential to be used in nanoparticles as well as biological systems.