Dithiafulvene and catechol as organic molecular building blocks for applied materials

This thesis reports the synthesis a series of novel dithiafulvenyl (DTF) compounds, and their characterization. This entails an investigation into their unique electronic properties, as well as their response to both chemical and electrochemical oxidation. This work expands upon previous work within the Zhao group to prepare bis-spiro compounds from DTFs, and works toward a mechanistic explanation for this process. Additionally, examination of DTF species unreactive to typical oxidative dimerization to tetrathiafulvalene (TTFV) using density-functional theory (DFT) optimization has elucidated the effect of resonance delocalization on the reactivity of the radical cation DTF toward TTFV formation. This thesis also reports the synthetic efforts toward a catechol-functionalized polysiloxane material for anticorrosion and antifouling marine coating additives. Several routes have been explored in attempts to obtain the target compound, including the Hiyama and Kumada coupling reactions. The difficulties faced in synthesis and the potential new avenues to pursue are discussed