| Acenes have been explored by a number of research groups in the field of organic electronics with a particular emphasis on transistor materials. This group has been actively studying acene-based organic semiconductors for more than a decade using a crystal engineering approach and has developed acene derivatives for applications in field-effect transistors, light-emitting diodes, and photovoltaics. In addition to organic electronics, crystal engineering has important applications in a number of other fields, quite notably in the design of metal-organic frameworks.;Chapters 2 and 3 of this dissertation focus on applying crystal engineering to the synthesis of acene derivatives for use as solid-state, long-wavelength fluorescent organic dyes in the field of biomedical imaging. More specifically, this work studied the synthesis and properties of dioxolane-functionalized pentacenes and hexacenes. One of these pentacene derivatives has already been demonstrated in biomedical imaging which may lead to improved treatment of tuberculosis. The dioxolane-functionalized hexacene is still under evaluation for bioimaging applications.;Chapters 4 and 5 focus on crystal engineering in relation to organic electronics. Chapter 4 deals with fine-tuning of crystal packing and demonstrated that small differences in molecular structure can result in significant changes to the solid-state structure which affects semiconductor properties. Finally, chapter 5 studies the use of singlet fission in photovoltaics and demonstrated that this process does occur in a solar cell incorporating a hexacene derivative. Pentadithiophenes were also synthesized for singlet fission photovoltaics, but they have yet to be studied further.;KEYWORDS: Crystal Engineering, Biomedical Imaging, Acenes, Singlet Fission, Organic Semiconductors. |
