Synthesis of novel redox-active building blocks for supramolecular and materials chemistry

McDonald, Niall A. (2010) Synthesis of novel redox-active building blocks for supramolecular and materials chemistry. PhD thesis, University of Glasgow.

Abstract

Supramolecular chemistry involves the study of noncovalent interactions that take place between molecules. A supramolecule or host-guest complex is formed when a noncovalent
binding or complexation event occurs between two such molecules. Hydrogen bonds, electrostatics, π-stacking, hydrophobic effects and Van der Waals forces are all types of noncovalent interactions. The incorporation of redox active molecules into supramolecular systems is desirable, as they can be used as a convenient way of observing changes in a systems environment.

This study involves the synthesis of a range of different redox active molecules, incorporated into supramolecular or materials devices. Firstly, two novel polymerisable flavin monomers have been synthesised. Attempts to polymerise these monomers, followed by characterisation to determine the physical and electronic properties were carried out. Secondly, a porphyrin system capable of binding to a flavin moiety has been prepared, and these complexes have been studied using physical and electrochemical techniques. This system offers an insight into the relationship between the porphyrin and flavin in nature. Furthermore, it would also serve to show how metals in close proximity to the flavin moiety can affect its supramolecular and electrochemical properties. A redox active ureidopyrimidinone system, capable of forming very strong dimer complexes, has been synthesised. This is able to tautomerise in solution, and using a combination of physical and electrochemical techniques, these supramolecular interactions have been studied. A polymer also displaying these properties has also been prepared and studied to understand the supramolecular properties it possesses.

The results of this study will hopefully contribute significantly to the body of chemical research in the area of supramolecular and materials chemistry, with a variety of interesting results and scope for further expansion of these projects.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Porphyrin, organic conducting polymers, polythiophene, redox active ureidopyrimidinone
• Subjects: Q Science > QD Chemistry; Q Science > Q Science (General)
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Cooke, Dr. Graeme
• Date of Award: 2010
• Embargo Date: 8 October 2016
• Depositing User: Mr Niall / NM McDonald
• Unique ID: glathesis:2010-1904
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 24 Jun 2010
• Last Modified: 27 Jun 2016 10:27
• URI: https://theses.gla.ac.uk/id/eprint/1904