Synthesis and Functionalization of Bullvalene-Derived Materials
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Sweningson, Sterling Jon
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Abstract
This thesis focuses on the synthesis and functionalization of bullvalene molecules for use in soft materials. Previous synthetic efforts towards bullvalene have found high-yielding procedures, but lack thermally stable functional handles which limit its use as a building block for bulk materials. Chapter 1 provides a background of the properties and synthetic history of bullvalene, and its previous applications in sensor molecules. Chapter 2 outlines the initial attempts to synthesize, functionalize, and polymerize bullvalene which proved unsuccessful but are important to outline. Chapter 3 introduces bullvalene anhydride as an important functional handle for installing substituents in an efficient manner, and also outlines the phenomenon of intramolecular hydrogen-bonding in bullvalene molecules. Chapter 4 describes the use of bullvalene monomers as fluxional cross-linkers in networks and the larger effect of fluxionality in materials science. Chapter 5 delves into the installment of mesogenic substituents onto bullvalenes and the corresponding properties of bullvalene liquid crystals. Chapter 6 concludes this thesis and describes the future directions of the project based on preliminary findings, other monomer designs, and the potential of bullvalene in materials outside of liquid crystals and polymers.
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2023-05-09
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Dissertation