Crystal Engineering of Boron Subphthalocyanine Derivatives Using Hydrogen and Halogen Bonding for Organic Electronic Applications

Boron subphthalocyanines (BsubPcs) are a class of aromatic bowl-shaped small molecules of interest for organic electronic applications such as organic solar cells. In solid state organic electronic devices, the orientation of the molecules and the spacing between them affect important material properties. In this thesis, the structure-property relationships between molecular structure, solid state arrangement and organic electronic device characteristics are explored for BsubPc derivatives. Hydrogen bonds and halogen bonds are of particular interest in the field of crystal engineering, due to the strength and directionality of these intermolecular interactions. The ability of BsubPcs to form hydrogen and halogen bonds was systematically explored. BsubPc derivatives which display either halogen or hydrogen bonds in their solid state arrangement were incorporated into organic solar cell devices and their thin film properties were studied in order to investigate the relationship between solid state arrangement and material properties.Ph.D