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.