Achieving Olympicene Functionalization Three Ways

Abstract

Polycyclic aromatic hydrocarbons (PAHs) and their derivatives are of interest in many fields, from materials science to supramolecular chemistry. 6H-Benzo[cd]pyrene, or olympicene, is a PAH bearing a central sp³-carbon bridge. We sought methods to modify this center position while maintaining stable tetrahedral geometry. Here, we characterize reactivity patterns of three olympicene core starting materials, with two of the three leading to center functionalization of the olympicene core, including the first use of 5H-benzo[cd]pyren-5-one as an olympicene synthon.