My research probes the structure-property relationship of organic semiconductors in order to gain insight into effectively tuning materials. Rubrene is one of the best organic semiconductors to date due to the pi-stacking that occurs when rubrene is crystallized in the orthorhombic setting. We sought to explore the effect of limited and extensive substitution on rubrene on its solid state and resulting electrical properties. We anticipated that selectively substituting rubrene would allow us to manipulate the solid-state structure to maintain the pi-stacking while changing the packing in other ways. Calculations have indicated that the surrounding layers of the rubrene crystal structure polarize charge moving through the crystal, acting as a trap. We propose that if the layers could be pushed further apart, the charge carrier mobility could be increased. Alternatively, fully substituting the rubrene structure with deuterium or fluorine may significantly influence the electrical properties while minimally changing the solid-state packing. My projects focus on exploring the effects of these substitutions on the solid-state structure of rubrene derivatives through the synthesis and crystallization of these compounds so that they might be studied in electrical devices.
University of Minnesota Ph.D. dissertation. September 2013. Major: Chemistry. Advisor: Christopher Douglas. 1 computer file (PDF); xvii, 399 pages.
Synthesis and Crystal Design of Rubrene Derivatives for Use in Organic Electronics.
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