title: Using antiaromaticity to illuminate aromaticity during a research career with undergraduates.
abstract: Antiaromatic species tend to be among the least well-studied and understood group in organic chemistry, primarily because their anticipated instability dissuaded most chemists from exploring their behavior. A research project that was intended to form three-dimensional aromatic dications resulted instead in a set of antiaromatic dications from oxidation of fluorenylidene derivatives. These dications can be modified in ways that help illuminate factors that affect both antiaromaticity and aromaticity. The characterization of these species, as well as antiaromatic dianions, through magnetic, energetic, and structural properties is described along with the relationships between these properties. Because this work represents contributions almost exclusively from undergraduate researchers, and because many readers of the Journal may not have a great deal of experience in this environment, I also include some thoughts about the opportunities and challenges of undergraduate research.
authors.affiliation: Department of Chemistry, Trinity University, San Antonio, Texas 78212, USA. nmills@trinity.edu
authors.forename: Nancy
authors.initials: N
authors.lastname: Mills