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Synthesis and Properties of Graphyne Model Compounds and an Electrochemical Study of Substituted Pentacenes Open Access


Other title
Type of item
Degree grantor
University of Alberta
Author or creator
Murray, Adrian H
Supervisor and department
Veinot, Jonathan (Chemistry)
Tykwinski, Rik (Chemistry)
Examining committee member and department
Stryker, Jefferey (Chemistry)
Baumgartner, Thomas (Chemistry, University of Calgary)
Clive, Derrick (Chemistry)
Meldrum, Alkiviathes (Physics)
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
The work described in this thesis focuses on two central topics: (1) the synthesis of carbon-rich macrocycles as model compounds of the carbon allotrope graphyne and the study of their electronic properties, and (2) the electrochemical investigation of the properties of substituted pentacene molecules. To this end, Chapter 1 first offers an introduction to conjugated organic materials, focusing on acetylene-rich macrocycles. Subsequently, the theoretical structures of graphyne are introduced, and their potential properties described. Previous synthetic efforts to prepare model compounds for graphyne are also discussed. Chapter 2 focuses on the synthesis of 12,12,12-graphyne. Described first are the syntheses of small molecules based on four molecular scaffolds: (1) aryl triazenes, (2) dibromoolefins, (3) tetraethynylethenes, and (4) vinyl triflates. These molecules are characterized using standard methods, including 1H and 13C NMR, IR, and mass spectrometries. These molecules are then used as building blocks toward the synthesis of expanded radialenes, which would serve as model compounds for 12,12,12-graphyne. Chapter 3 focuses on the use of small molecules prepared in Chapter 2 as building blocks toward a series of radiaannulene oligomers, which serve as model compounds for 6,6,12-graphyne. Several synthetic routes are explored in an effort to optimize preparation of the series of radiaannulenes. The products are characterized by 1H and 13C NMR, IR and mass spectrometries, as well as by X-ray crystallography. The electronic properties are investigated using UV-vis spectroscopy and cyclic voltammetry to provide insight into the potential properties of 6,6,12-graphyne. Chapter 4 focuses on the electrochemical properties of substituted pentacenes. A brief introduction to pentacene and functionalized pentacene is provided. The syntheses of several pentacene derivatives is outlined, and the synthesis of conjugated pentacene-thiophene molecules is described. The effect of the substituents on the HOMO and LUMO energy levels and band gaps of the pentacene molecules is described, based on results from cyclic voltammetry. The thesis concludes with a brief summary, an outlook for the synthesis graphyne model compounds, and a description of how radiaannulenes might serve as useful materials in the synthesis of other conjugated organic molecules
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication
Lehnherr, D.; Murray, A. H.; MacDonald, R.; Ferguson, M. J.; Tykwinski, R. R. Chem. Eur. J. 2009, 15, 12580–12584.Lehnherr, D.; Murray, A. H.; MacDonald, R.; Tykwinski, R. R. Angew. Chem. Int. Ed. 2010, 49, 6190–6194.

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