The Chemical Synthesis Program of the Chemistry Division of the NSF supports the project by Professor Thomas R. Hoye. Professor Hoye is a faculty member in the Department of Chemistry at the University of Minnesota. He is developing new chemical reactions that allow for the synthesis of novel molecules known as polycylic aromatics. These molecules are valuable for a variety of reasons, one being their potential for use in optoelectronic devices such as the organic light emitting diodes (OLEDs) and photovoltaic cells that are used in energy efficient displays, lighting units, and for the conversion of solar energy into electricity. By developing a fundamental understanding of the new reactions used to make polycyclic aromatics, Professor Hoye and his coworkers may push the chemical reactions toward the synthesis of compounds having previously unknown chemical structures and, in the future, build new materials with improved properties. A number of significant broader impacts of benefit to a wide group of stakeholders result from the project. Of particular note are research opportunities for undergraduate research students, a tutorial on the practical separation of complex organic mixtures, and new extensions of the Minnesota State Fair exhibit on "Sustainable Polymers."
Professor Hoye's research group is capitalizing on the tremendous potential for the hexadehydro-Diels-Alder (HDDA) reaction cascade to provide for the rapid chemical synthesis of manifold classes of highly conjugated polycyclic aromatics. Some are of value to the field of organic electronic and photonic materials research. Collaborations are in place to pursue early phases of such development. It is the methods and strategies for the syntheses of such compounds that are the most important 'products' that are emerging from this project. Preliminary results demonstrate that the synthetic routes are often remarkably short and efficient. New and fundamentally important mechanistic knowledge is also emerging. Advances in the benzyne chemistry include new aspects of cycloaddition reactions, two-directional benzyne trapping, and controlled oligomer synthesis. A process dubbed the 'domino-HDDA reaction' is particularly intriguing. Professor Hoye holds major teaching awards that recognize his career-long commitment to the education of students at both the undergraduate and graduate levels. Outreach activities supported by this project benefit chemistry research students at multiple levels and contribute to the education of the public in the arenas of green chemistry and sustainable polymers. The scientific advances have the possibility of opening new avenues for pursuit by materials scientists who use organic electronic and photonic compounds in the settings of light-emitting diodes, photovoltaics, and solar cells. These applications have a large potential for societal impact.