Electronic materials have been revolutionized by recent advances in synthetic chemistry through the incorporation of organic semiconductors, replacing traditional semiconducting materials. Organic light-emitting diodes (OLEDs) and field-effect transistors (FETs) are a few of the many technologies that incorporate these organic semiconductors. Compared to traditional inorganic semiconductors, organic semiconductor materials have a number of advantages, including facile production and the ability to function on flexible substrates. Various heterocycles, specifically furans, have been incorporated into conducting polymers, exhibiting semiconducting properties. Unlike acyclic organic conductive polymers, polyheterocycles exhibit high environmental stability, in addition to synthetic versatility. Incorporation of furans into conductive polymer systems also provides the benefit of a renewable feedstock of this material from biofuels production processes. However, furans are largely unexplored and further research is necessary for commercial application of these furan materials. This paper will focus on the role of furans in electronic devices, previous research on furan organometallic precursors for use in conductive polymers, and the synthesis of some novel Group VII furanyl organometallic complexes. These syntheses began with some acid chloride and the appropriate stoichiometric quantity of cyclopentadienyl anion to form the desired fulvene product. Formation of the metallated fulvene system was accomplished by reaction with thalium(I) ethoxide, and then subsequent reaction with manganese pentacarbonyl bromide. Formation of various fused-ring complexes was achieved through ring closure by hydrazine hydrate. The overall goal of this research is to develop novel synthetic pathways of furanyl and other aromatic fulvene organometallic complexes that can serve as precursors for conductive polymer systems.
Semester/Year of Award
Darrin L. Smith
Restricted Access Thesis
Mazzotta, Michael G., "The Synthesis of Some Novel Group VII Furanyl Organometallic Complexes" (2012). Honors Theses. 27.