B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O2 Sensitization

The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B–N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted polycyclic aromatic hydrocarbons show large bathochromic shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O2 without the need for an external photosensitizer, resulting in selective and reversible formation of the corresponding endoperoxides.