Return to search

Heteroatom Substitution within Indenofluorenes

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This dissertation includes previously published and unpublished coauthored material.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

Identiferoai:union.ndltd.org:uoregon.edu/oai:scholarsbank.uoregon.edu:1794/20402
Date27 October 2016
CreatorsMarshall, Jonathan
ContributorsPluth, Michael
PublisherUniversity of Oregon
Source SetsUniversity of Oregon
Languageen_US
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
RightsCreative Commons BY-NC-ND 4.0-US

Page generated in 0.0019 seconds