With this Research in Undergraduate Institutions (RUI) award, the Organic and Macromolecular Chemistry Program supports the research of Professor Cheryl D. Stevenson of the Department of Chemistry at Illinois State University in Normal IL. This research will involve investigations of annulenes, cyclic systems with conjugated double bonds, and monoannulynes, annulenes containing a triple bond. These unusual molecules have properties that are dependent on the number of electrons in the conjugated system. Systems with 4n+2 (n = 1,2,3 ...) electrons are aromatic and stable while systems with 4n electrons are antiaromatic and generally unstable. In this research, Professor Stevenson will generate a series of highly reactive antiaromatic annulenes and monoannulynes and study the properties of these interesting species, which have received little attention. These unstable molecules will be investigated by low temperature NMR spectroscopy and reduced to their more stable radical anions, which will be studied by ESR spectroscopy. These investigations will be accompanied by sophisticated computational studies involving spectral simulation and quantum mechanical investigations. Much of this work, which has been ongoing in the PI's laboratory for many years, will be carried out by undergraduate students. In this way the project will serve as a training ground and inspiration for young scientists who will be encouraged to pursue careers in science.
