Synthesis of fluoromodified carbon rich electron acceptors and exploration of their structural, electronic, and device properties

DeWeerd, Nicholas J., author
Strauss, Steven H., advisor
Shores, Matthew P., committee member
Ackerson, Chris J., committee member
McCullagh, Martin J., committee member
Gelfand, Martin P., committee member
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The electronic and structural characterization of fluoro-modified carbon-rich compounds is critical to the successful implementation of these materials by physicists, biochemists, materials scientists, medicinal chemists, and most significantly for this work, organic electronics chemists. By adding powerful electron-withdrawing groups, the electron acceptor and solid-state structural properties of carbon rich substrates such as polyaromatic hydrocarbons (PAHs) and fullerenes can be improved, making these derivatives attractive semiconductor materials for organic electronics applications. This work will discuss research which has focused on expanding the library of electron acceptor compounds, elucidating the electronic and structural properties of those compounds, and exploring their physicochemical properties, focusing on properties that are important for the performance of organic electronic devices. This was accomplished by exploring reaction conditions which had not been previously reported at pressures and temperatures exceeding the operational limits of conventional reactors, developing purification methods that allow for chromatographic separation of constitutional isomers, and structural characterization of those purified materials by mass spectrometry, NMR, and most importantly X-ray crystallography. As a complement to this research, the stability of organic electronic active layers was studied to better understand how organic semiconductor active layer's degradation affects device performance over time and to better inform which active layer material properties should be pursued. Based on those findings and literature precedent, one family of compounds, C60 and C70 fauxhawk fullerenes, found to have favorable characteristics were then utilized in OFET devices as n-type semiconductors resulting in record-setting charge carrier mobilities.
Includes bibliographical references.
2020 Summer.
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