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From Quadrannulene To Septulene
AdvisorKing, Benjamin T.
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The focus of this dissertation is the synthesis and properties of novel polycyclic aromatic hydrocarbons (PAHs). The first chapter covers introduction to PAHs, aromaticity, circulenes, and kekulenes.The second chapter describes the synthetic efforts toward circulene and complements chapter 3. The synthesis of circulene was achieved using cyclotrimerization of precursor alkyne.The third chapter covers the synthesis and properties of the first stable circulene. The predicted and experimental properties of circulene suggested its radialene nature, with four double bonds emanating from a central four-membered ring. These findings suggest that the square may join the pentagon as a motif for viable fullerenes. The fourth chapter describes the applicability of zirconium-mediated and palladium catalyzed biphenylation reactions to the synthesis of soluble PAHs. All synthesized PAHs in this chapter are soluble in common organic solvents. This chapter also compares the effectiveness of zirconium-mediated and palladium-catalyzed coupling reactions.The fifth chapter covers the first synthesis of heptagonal analogue of kekulene, kekulene or septulene. The properties of septulene were found to be strikingly similar to kekulene despite fundamental difference in their kekúle structures. This similarity highlights the utility of Clar's sextet rule.The sixth chapter describes the synthetic efforts toward two-dimensional polymers (2DPs) based on a fluorinated monomer with three anthracene blades. We intent to use the photodimerization of anthracene blades as the key step. Two synthetic routes have been explored for the synthesis of the monomer. Both routes yielded small quantities of the monomer. The preliminary results indicate photopolymerization of the monomer.The seventh chapter is the graphical abstract of crystallographic information files. All structures shown in this chapter are publishable.