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Synthesis of Luminescent Tellurophenes for Optoelectronic Applications
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- Author / Creator
- Torres Delgado, Willliam
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With the goal to form stable, solid state tunable emitters at room temperature, the work within this thesis describes the synthesis of both symmetric and unsymmetric tellurophenes along with the study of their optoelectronic properties in solution and in the solid state. Chapter 2 describes the synthesis of a series of tetraborylated thiophenes, selenophenes and tellurophenes via transmetallation reactions. The optical properties of the series were studied by UV-vis spectroscopy, fluorescence spectroscopy and cyclic voltammetry, as well as using theoretical calculations (TD DFT). Luminescence from tetraborylated/diborylated tellurophenes was studied under argon and in aerated conditions, given O2-dependent phosphorescence in solution and the solid state. Chapter 3 reports the synthesis of new borylated and bromide-functionalized tellurophenes via selective protodeboronation reactions of tetraborylated tellurophenes under thermal and microwave conditions and via exchange reactions using copper dibromide. The protodeboronation of tetraborylated chalcogenophenes (thiophene, selenophene and tellurophene) is described and their respective 3,4-diborylated products featured non-emissive properties in the solid state and in solution. It is expected that both new borylated and brominated tellurophenes will serve as building blocks for the further preparation of conjugated polymers. Chapter 4 features the synthesis of symmetric and unsymmetric aryl-tellurophenes through Suzuki-Miyaura and Sonogashira cross coupling reactions. The goal was to tune the phosphorescent properties via modification of the central tellurophene in the 2,5-positions with electron donating/withdrawing substituents. It was found that the electron withdrawing group, m-(CF3)2C6H3, attached to the tellurophene forms a couple acceptor-donor-acceptor with intense phosphorescent emission. This study showed the possibility of achieving phosphorescence using readily available di-arylated tellurophenes.
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- Graduation date
- Fall 2017
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- Type of Item
- Thesis
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- Degree
- Doctor of Philosophy
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- License
- This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.