Tetrathiafulvalene as a molecular building block in various systems

Leem, Soojung Clara
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Tetrathiafulvalene (TTF), a classic electron rich donor system, has received renewed attention within the supramolecular and complex ligand chemical communities. As the result of recent synthetic advances, TTF and its derivatives have been incorporated into many complex receptor systems that have been explored as binding agents, sensors, and electron transfer models. In this thesis, the synthesis and the attempted use of TTF moieties in the construction of systems that could see a variety of applications will be described. In the first chapter, a brief overview of the theoretical and historical background of TTF is given with the focus on the redox properties of TTF. The second chapter details the design of, and synthetic attempts to prepare a new TTF-based anion receptor. This latter system was designed to allow a well-recognized anion binding motif to be attached to a TTF core. However, the desired target was not obtained. The third chapter describes the author’s contribution to the development of a self-assembled system comprised of a TTF-substituted macrocycle and a functionalized fullerene. In this ensemble, two heteroditopic monomers combine to create a chemically and electrochemically responsive supramolecular oligomeric product.