Heteroatom Substitution within Indenofluorenes
| dc.contributor.advisor | Pluth, Michael | |
| dc.contributor.author | Marshall, Jonathan | |
| dc.date.accessioned | 2016-10-27T18:06:28Z | |
| dc.date.issued | 2016-10-27 | |
| dc.description.abstract | 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 This dissertation includes previously published and unpublished coauthored material. | en_US |
| dc.description.embargo | 10000-01-01 | |
| dc.identifier.uri | https://hdl.handle.net/1794/20402 | |
| dc.language.iso | en_US | |
| dc.publisher | University of Oregon | |
| dc.rights | Creative Commons BY-NC-ND 4.0-US | |
| dc.subject | Antiaromaticity | en_US |
| dc.subject | Heteroatom | en_US |
| dc.subject | Indenofluorene | en_US |
| dc.subject | Organic electronics | en_US |
| dc.title | Heteroatom Substitution within Indenofluorenes | |
| dc.type | Electronic Thesis or Dissertation | |
| thesis.degree.discipline | Department of Chemistry and Biochemistry | |
| thesis.degree.grantor | University of Oregon | |
| thesis.degree.level | doctoral | |
| thesis.degree.name | Ph.D. |
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