Synthesis and Physical Study of Perylene and Anthracene Polynitrile as Electron Acceptors.

Attaching electron-withdrawing nitrile groups to π-conjugated systems is an effective approach toward electron acceptors. By combining various cyanation methodologies, perylene and anthracene polynitriles with up to eight nitrile substituents on one aromatic scaffold were synthesized. This strategy produces stable electron acceptors with lowest unoccupied molecular orbital (LUMO) levels comparable to benchmark acceptors. A very stable octanitrile anion was also produced serendipitously. Reactivity patterns of these acceptors were rationalized by density functional theory (DFT) calculation.