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Carbon-carbon bond formation methods for the preparation of shape-persistent architectures

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Title: Carbon-carbon bond formation methods for the preparation of shape-persistent architectures
Author(s): Finke, Aaron D.
Director of Research: Moore, Jeffrey S.
Doctoral Committee Chair(s): Moore, Jeffrey S.
Doctoral Committee Member(s): White, Maria C.; Zimmerman, Steven C.; Gruebele, Martin
Department / Program: Chemistry
Discipline: Chemistry
Degree Granting Institution: University of Illinois at Urbana-Champaign
Degree: Ph.D.
Genre: Dissertation
Subject(s): Shape-persistent macrocycles carbon-carbon bond formation C-H activation palladium supramolecular crystallography
Abstract: Carbon-rich, conjugated organic scaffolding is a popular basis for functional materials, especially for electronic and photonic applications. However, synthetic methods for generating these types of materials lack diversity and, in many cases, efficiency; the insistence of investigators focusing on the properties of the end product, rather than the process in which it was created, has led to the current state of the relatively homogeneous synthetic chemistry of functional organic materials. Because of this, there is plenty of room for improvement at the most basic level. Problems endemic to the preparation of carbon-rich scaffolding can, in many cases, be solved with modern advances in synthetic methodology. We seek to apply this synthesis-focused paradigm to solve problems in the preparation of carbon-rich scaffolds. Herein, the development and utilization of three methodologies: iridium-catalyzed arene C-H borylation; zinc- mediated alkynylations; and Lewis acid promoted Mo nitride-alkyne metathesis, are presented as improvements for the preparation of carbon-rich architectures. In addition, X-ray crystallographic analysis of two classes of compounds are presented. First, an analysis of carbazole-containing arylene ethynylene macrocycles showcases the significance of alkyl chain identity on solid-state morphology. Second, a class of rigid zwitterionic metal-organic compounds display an unusual propensity to crystallize in the absence of inversion symmetry. Hirshfeld surface analysis of these crystalline materials demonstrates that subtle intermolecular interactions are responsible for the overall packing motifs in this class of compounds.
Issue Date: 2011-05-25
Rights Information: Copyright 2011 Aaron D. Finke
Date Available in IDEALS: 2011-05-25
Date Deposited: 2011-05

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