Design and synthesis of bi-functional, 1,2,4,5-tetraoxane-based molecular wires and their application in microbial fuel cells

摘要

Chapter 1 begins with a general introduction to the main aspects of this work: Firstly, a species of electrogenic bacteria, Geobacter sulfurreducens is introduced. Their ability to take part in extracellular electron transfer, the mechanisms by which this happens, and their involvement in electricity generation and bioremediation when applied in microbial fuel cells is discussed; Secondly, microbial fuel cells (MFCs) as an alternative method of electricity generation to fossil fuels, their methods of operation and their potential for use in the treatment of wastewater is briefly reviewed; Finally, antimalarial drugs (including their semi-synthetic and synthetic analogues) and their mechanisms of action are presented. The possibility of exploiting them as a template for bi-functional molecular wires that are capable of tethering bacteria to carbon and/or gold electrode surfaces is discussed in detail. Chapter 2 outlines our efforts towards novel analogues of synthetic antimalarials, dispiro-1,2,4-trioxolanes, for use as bi-functional molecular wires. These are shown to be capable of immobilising heme on carbon and gold surfaces via appropriate functional groups. Chapter 3 discusses our efforts towards novel analogues of synthetic antimalarials, dispiro-1,2,4,5-tetraoxanes for use as bi-functional molecular wires. The syntheses of many novel precursors; namely functionalised adamantanone derivatives and their corresponding tetraoxanes are presented. Synthetic routes towards bi-functional tetraoxane molecular wires have been extensively optimised and the incorporation of functional groups that are compatible with carbon/gold surfaces has been attempted. Chapter 4 briefly introduces the design and synthesis of β-turn mimetics and the synthesis of chiral enamine N-oxides. Chapter 5 details the experimental procedures.