The inclusion of atoms other than carbon into the framework of polycyclic conjugated hydrocarbons can have profound effects on the properties of the resultant compounds. Substitution of acenes with nitrogen-, oxygen-, and sulfur-containing rings has long been used as a strategy to alter the HOMO and LUMO energy levels of a compound and direct the solid-state morphology. In this thesis, I present my work in extending heteroatom substitution into the class of compounds known as indenofluorenes.
Chapter I serves as an overview of indenofluorenes and related compounds with a special focus on the redox properties of these materials. Chapter II covers the synthesis and characterization of two selenophene-containing indenofluorene analogues. Chapter III discloses a new synthetic method for the preparation of unsymmetrical indenofluorenes and discusses the unusual reactivity of the dione precursors. Chapter IV is a comprehensive study of indacenodibenzothiophenes. This chapter investigates how heteroatom substitution affects the antiaromaticity of the indacene core and presents a detailed optoelectronic, computational, solid-state and materials study of a series of indacenodibenzothiophene derivatives. Chapter V presents my work towards the synthesis of the final unknown indenofluorene isomer, indeno[1,2-a]fluorene. Appendices A and B discuss my work done as part of Professor Shih-Yuan Liu’s research group at the start of my graduate career.
This dissertation includes previously published and unpublished coauthored material. / 10000-01-01
| Identifer | oai:union.ndltd.org:uoregon.edu/oai:scholarsbank.uoregon.edu:1794/20402 |
| Date | 27 October 2016 |
| Creators | Marshall, Jonathan |
| Contributors | Pluth, Michael |
| Publisher | University of Oregon |
| Source Sets | University of Oregon |
| Language | en_US |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Rights | Creative Commons BY-NC-ND 4.0-US |
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