CHEMISTRY Syntheses of Asymmetric Dehydrobenzoannulenes

Syntheses of Asymmetric Dehydrobenzoannulenes. Virgina Perleberg-Nobbe, Wil Talbert,
Bobby Joe Wherle, Brittany Cramer, Andrew Price, Katie Sullivan, Kaitlin Cahill, Stephen
Hendricks and KC Russell. Department of Chemistry, Northern Kentucky University, Highland
Heights, KY 41099.
Dehydrobenzonnulenes (DBAs) are completely conjugated cyclic compounds made from
aromatic linked by triple bonds. DBAs incorporating aromatic rings often possess spectroscopic
properties that make them ideal candidates for the development of environmental sensor
technologies. Placement of electron donor and electron withdrawing groups on the periphery of
an annulene results in a push-pull system which affects its spectroscopic properties. The Russell
Research Group has previously reported the synthesis of a series of symmetric annulenes. The
focus of this research is to synthesize a series of asymmetric DBAs, giving new isomers lacking
symmetry with respect to the electron donating oxygen and the electron withdrawing nitrogen
atoms. Thus far, three of the four dimmers and one of the four trimers necessary to make the
four isomeric, asymmetric annulenes have been synthesized.