Synthesis and Explorations of Indenofluorenes and Related Molecules
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Small perturbations upon the bonding of polycyclic conjugated hydrocarbons (PCH) lead to drastic changes of the properties. Despite being extensively studied for decades, there are numerous variants that remain unknown. Many PCHs are of interest for application in organic electronics; namely organic photovoltaics, organic field effect transistors and non-linear optics. Although many properties of these compounds can routinely be calculated to within desired accuracy, their morphology in the solid state remains in the experimentalists' realm. The solid state morphology of these compounds dictates how easily charge moves, a very important parameter for devices. Organic compounds can range from insulators to conductors, and making organic compounds that are semiconductors is a difficult task. This dissertation covers my progress in research in the synthesis and calculations of some of new PCHs. Chapter I serves as an overview of the progress in our laboratory working with indenofluorenes and structurally related motifs. Chapter II covers the first report of a well characterized atmospherically stable indeno[1,2-b]fluorene which was the groundwork for all further research. Chapter III discloses the synthetic advances that have been made in regards to the indeno[1,2-b]fluorene diones and a number of derivatives synthesized. Chapter IV encompasses fundamental studies of the reduced states of the indeno[1,2-b]fluorene scaffold. Chapter V details the observations of the photo excited state of indenofluorene and related molecules, providing a rationale why these are non-emissive molecules. Chapter VI discusses the synthesis and electronic properties of the expanded indenofluorene scaffold, fluoreno[4,3-c]fluorene. This dissertation includes previously published and unpublished co-authored material.