Synthesis and properties of π-stacked phenylene ethynylene oligomers with a 1,8- substituted naphthalene bridging scaffold
Carson, Bradley Edward
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The field of molecular electronics includes the study of conjugated oligomers and polymers that have significant potential for use in devices such as light emitting diodes (LEDS), field effect transistors (FETS), and photovoltaic solar cells. These materials may replace inorganic semiconductors in these devices, Achieving better device performance through lowering the band-gap and achieving higher field effect mobilities will benefit from a greater fundamental understanding of charge transfer through the aromatic subunits. π-stacking of segments of conjugated polymers has been identified as a key feature that influences the charge transfer through semiconducting organic materials. Optimizing the molecular architecture of conjugated polymers has the potential to provide materials with better charge mobility. While devices might benefit from materials that take advantage of π-stacking, access to π-stacked structures presents a synthetic challenge. 1,8-Disubstituted naphthalenes may serve as simple covalent bridging scaffolds which might hold conjugated oligomers in a π-stacked arrangement. The research described in this thesis focuses on the synthesis of well-defined phenylene ethynylene oligomers coupled to naphthalene to serve as experimental models of closely π-stacked aromatic units in conjugated polymers. The π-stacked molecules reported in this dissertation are characterized by NMR, IR, and mass spectrometry. The effects of π- stacking on the structure and behavior of conjugated oligomers are determined by X-ray crystallography, spectroscopy, and electrochemistry.