Electronic Materials: An Antiaromatic Propeller Made from the Four‐Fold Fusion of Tetraoxa[8]circulene and Perylene Diimides

The synthesis of an antiaromatic tetraoxa[8]circulene annulated with four perylene diimides (PDI), giving a dynamic non-planar π-conjugated system, is described. molecule contains 32 aromatic rings surrounding one formally planarized cyclooctatetraene (COT). intense absorption (ϵ=3.35×105 M−1 cm−1 in CH2Cl2) and emission bands are assigned to internal charge-transfer transitions the combined PDI-circulene π-system. spectroscopic data supported by density functional theory calculations, nuclear independent chemical shift calculation indicate that COT has increased aromaticity reduced state. Electrochemical studies show compound can reversibly reach tetra- octa-anionic states reduction PDI units, deca-anionic state central ring. material functions effectively bulk hetero junction solar cells as non-fullerene acceptor, reaching power conversion efficiency 6.4 %.