Title:
Multi-tiered Conjugated Oligomers as Models to Mimic Pi-Pi Interactions in Semiconducting Conjugated Materials

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Johns, Ashley Elisabeth
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Collard, David M.
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Abstract
The electronic structure of semiconducting π-conjugated materials continues to attract interest through both experimental and theoretical approaches. To explore the effects of intermolecular interactions between conjugated systems, we have embarked on an examination of the electronic structure of a series of molecules in which conjugated segments are held in a stacked arrangement. This arrangement mimics face-to-face packing of segments in the crystalline region of conjugated polymers. We report the use of [2.2]paracyclophane as a scaffold to create multi-tiered oligo(phenylene ethynylene)s. By substituting [2.2]paracyclophane in a pseudogeminal (pg) pattern with oligo(phenylene ethynylene)s, conjugated segments are held atop one another in a stacked manner consisting of a number of tiers. We have also explored the use of 1,8-disubstituted anthracene as a molecular scaffold to hold oligo(phenylene ethynylene) segments in a stacked arrangement. One-tier, two-tier, and three-tier structures were prepared. The effects of π-π stacking on electronic structure were studied through multiple methods. The oligomers are characterized using UV-Vis and fluorescence spectrometry and by voltammetry techniques to determine the evolution of optoelectronic properties as conjugated oligomers are assembled into multi-tiered architectures.
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2021-09-28
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Dissertation
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