Crystal Engineering of Asymmetric and Pyrene Fused Annulenes for Use in Organic Electronic Materials
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Year of Publication
Master of Science (MS)
Arts and Sciences
John E. Anthony
Since the development of TiPS Pentacene, the use of trialkylsilylethynyl groups has become a commonly utilized moiety for stabilizing, solubilizing, and directing crystal packing of acenes and acene-like compounds, leading to the development of a well-defined series of trends that aid in the prediction of crystal packing for the development of organic semiconducting materials. While these trends have been extensively studied in mainly symmetric linear systems, it is important to determine how, if at all, asymmetry of the aromatic core affects these well-defined trends. This constitutes the basis of Chapter 2, which explores the crystal engineering and physical properties of a novel set of heteroacenes.
In Chapter 3, we address the effects of dynamic disorder within a crystalline network, and explore the ways in which this disorder can be mitigated through the use of directly silylated pyrene delimited acenes. By directly attaching trialkylsilyl groups to the pyrene spacer, we eliminate the need for highly flexible ethynyl linkages to separate the solubilizing groups from the aromatic backbone. This also allows us to further our understanding of the ways in which these trialkylsilyl solubilizing groups can direct packing and generate new and unique materials for potential uses as organic semiconducting materials.
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The synthetic efforts of this work were supported by the National Science Foundation under Cooperative Agreement No. 1849213.
Fregoso, Garrett, "Crystal Engineering of Asymmetric and Pyrene Fused Annulenes for Use in Organic Electronic Materials" (2022). Theses and Dissertations--Chemistry. 162.