1. Electron Acceptors Based on Cyclopentannulated Anthanthrenes
- Author
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Frédéric Lirette, Yachu Du, Jean-François Morin, Hope B. Lovell, and Kyle N. Plunkett
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Anthanthrene ,Organic Chemistry ,chemistry.chemical_element ,Orange (colour) ,Electron acceptor ,010402 general chemistry ,Electrochemistry ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,chemistry ,HOMO/LUMO ,Palladium - Abstract
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 cyclopenta-anthanthrene compounds possess reduced optical and electrochemical gaps (~0.9 eV) compared to anthanthrene derivatives and are electron acceptors with lowest unoccupied molecular orbital energies of ~ -3.4 eV to -3.9 eV.
- Published
- 2021