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Electron Acceptors Based on Cyclopentannulated Anthanthrenes

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journal contribution
posted on 04.01.2021, 16:07 by Yachu Du, Hope B. Lovell, Frédéric Lirette, Jean-François Morin, Kyle N. Plunkett
We demonstrate the preparation of anthanthrene derivatives with fused five-membered rings. These new derivatives are prepared by a palladium catalyzed cyclopentannulation reaction from precursors derived from the low-cost dye Vat Orange 3 (4,10-dibromoanthanthrone). The new cyclopentaanthanthrene compounds possess reduced optical and electrochemical gaps (∼0.9 eV) compared to anthanthrene derivatives and are electron acceptors with lowest unoccupied molecular orbital energies from ∼ −3.4 to −3.9 eV.