The field of molecular electronics includes the study of conjugated oligomers andpolymers that have significant potential for use in devices such as light emitting diodes(LEDS), field effect transistors (FETS), and photovoltaic solar cells. These materials mayreplace inorganic semiconductors in these devices, Achieving better device performancethrough lowering the band-gap and achieving higher field effect mobilities will benefitfrom a greater fundamental understanding of charge transfer through the aromaticsubunits. π-stacking of segments of conjugated polymers has been identified as a keyfeature that influences the charge transfer through semiconducting organic materials.Optimizing the molecular architecture of conjugated polymers has the potential toprovide materials with better charge mobility. While devices might benefit from materialsthat take advantage of π-stacking, access to π-stacked structures presents a syntheticchallenge. 1,8-Disubstituted naphthalenes may serve as simple covalent bridgingscaffolds which might hold conjugated oligomers in a π-stacked arrangement. Theresearch described in this thesis focuses on the synthesis of well-defined phenyleneethynylene oligomers coupled to naphthalene to serve as experimental models of closelyπ-stacked aromatic units in conjugated polymers. The π-stacked molecules reported inthis 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-raycrystallography, spectroscopy, and electrochemistry.
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Synthesis and properties of π-stacked phenylene ethynylene oligomers with a 1,8-substituted naphthalene bridging scaffold
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