RUI: The Role of Bond Localization in Antiaromaticity: Aromaticity/Antiaromaticity Continuum for Indenyl Systems

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Aromaticity is one of the bedrock concepts of organic chemistry yet the physical properties associated with aromaticity are under dispute. Those physical properties are being examined in a series of antiaromatic dications and dianions, reasoning that the ability of a property to reveal the antiaromaticity of a species with 4 n pi-electrons will allow us to assess whether it is particularly useful in demonstrating the aromaticity of a species with 4 n + 2 pi-electrons. Also being examined are dications and dianions that form an aromaticity/antiaromaticity continuum that allows the physical properties to be evaluated within the same carbon framework. The results of the experimental work are being correlated with the results of theoretical calculations that are also being carried out. As for the Broader Impacts, this research is being carried on exclusively by undergraduate students, with the technical support of a post-doctoral research associate. Because the PI specifically targets first year undergraduate students for participation in the project, the research experience has a much greater impact in the development of the students than if they started as seniors. Many of these students will choose to go on to graduate school in the chemical sciences as a result of this research project and the mentoring provided by the PI and this will have a very positive impact on the chemical workforce.