Part 1: Structure-Property Relationships of Regioregular Poly(3-alkylthiophene)s Bearing Branched Side Chains Part 2: Ferric Chloride-Promoted Oxidative Annulation of 3,3’,4,4’-Tetrahexyloxy-1,1’- biphenyl with Arenes as a Facile Route to Discotic Liquid Crystalline 2,3,6,7,11,12,15,16- Octakis(hexyloxy)diphenanthro[9,10-b:9',10'-d] heteroarenes

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COX-DISSERTATION-2023.pdf (9.7 MB)
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Cox, Bronson Evan
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Part 1: Structure-Property Relationships of Regioregular Poly(3-alkylthiophene)s Bearing Branched Side Chains Part 2: Ferric Chloride-Promoted Oxidative Annulation of 3,3’,4,4’-Tetrahexyloxy-1,1’-biphenyl with Arenes as a Facile Route to Discotic Liquid Crystalline 2,3,6,7,11,12,15,16-Octakis(hexyloxy)diphenanthro[9,10-b:9',10'-d]heteroarenes Bronson Cox 216 Pages Directed by Dr. David M. Collard Part 1: The first objective of this dissertation was to investigate the influence of branched side chains on the physical and optoelectronic properties of poly(3-alkylthiophene)s. The different branched side chains incorporated into these polymers included a methyl group on the 2-,3-,4-, and 5-positions of a hexyl side chain, and at the 2- and 6-positions on a decyl side chain, and the use of the 2-ethylhexyl side chain. In addition, we sought to ascertain whether the use of these branched side chains might give rise to a thermotropic liquid crystal phase, whereby the polymer could be processed in a fluid, ordered melt to attain control over the alignment of the backbone and thereby enhance charge transport. Part 2: The second objective of this dissertation was to investigate a novel and straightforward approach for synthesizing new diphenanthro-fused heteroarenes. We synthesized these compounds by FeCl3-promoted oxidative annulation of 3,3’,4,4’-tetra(alkyloxy)biphenyl with 2-bromothiophene or pyrrole. We characterized the physical and optoelectronic properties of the products by NMR, UV-vis, and fluorescence spectroscopies, as well as by DSC and POM.
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2023-04-25
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