Development of Synthetic Processes and Characterization of BsubPcs with High Crystal Densities for Application in Organic Photovoltaic Devices

• Main Author: Fulford, Mabel Victoria
• Other Authors: Bender, Timothy
• Language: en_ca
• Published: 2013
• Subjects: subphthalocyanine; boron; organic; photovoltaic; halo; dimer; oxygen; bridge; bridged; synthesis; 0542
• Online Access: http://hdl.handle.net/1807/35605

The original goal of this thesis was to develop process chemistry to yield boron subphthalocyanine (BsubPc) derivatives which were previously difficult to access. Retrospectively, it was found that these compounds show extremely high density crystal packing in comparison to other known BsubPcs, and thus this also became a focus of the thesis. A process to synthesize and purify fluoro-BsubPc was developed. This led to a detailed comparison of the physical and chemical properties of the three halo-BsubPcs in order to answer the question of which halo-BsubPc is appropriate for different purposes. Through this work, the previously unpublished crystal structure of the oxygen bridged dimer, µ-oxo-BsubPc, was found. A process was subsequently developed for the practical synthesis of µ-oxo-BsubPc for use in vacuum deposition and a number of µ-oxo-BsubPc crystal polymorphs were found and analyzed. The properties of this group of compounds are discussed in the context of other known BsubPcs.