Explorations of controted polycyclic aromatics as electronic materials

This thesis describes the design, synthesis, characterization, and application of organic molecular materials made from strained polycyclic aromatic compounds. The strain in the molecular subunits induces non-planar structures. We coined the term “contorted aromatics” to describe these molecules. Contorted polycyclic aromatic hydrocarbons (PAHs) are not only structurally intriguing, but also promising small active molecules for organic electronic devices. This thesis explores the contorted PAHs in two directions, (1) making c-PAHs with high enantiomeric purity and (2) studying c-PAHs with expanded size, for desirable physical, chemical, and electronic properties. The synthesis and chiral resolution of trichloro c-hexabenzocorones (c-HBCs) stereoisomers in Chapter 2 enables the study of conversion barrier in expanded aromatic systems with adjacent cove-units. We also rationalized the formation of thermodynamic stereoisomers and kinetically trapped stereoisomers with density functional theory (DFT) calculations. The organic film effect transistors (OFETs) fabricating from racemic trichloro c-HBC are photo-responsive, suggesting enantiopure OFETs may have potential application in dete