Synthesis and structure of a highly fluorinated 7-bora-7H-benzo[de]anthracene

1,8-Dilithionaphthalene·tmeda reacts with bis(pentafluorophenyl)boronfluoride·Et2O in diethylether to afford 7-pentafluorophenyl-8,9,10,11-tetrafluoro-7-bora-7H-benzo[de]anthracene (1) in moderate yield. Compound 1, which features a boron atom incorporated in a fused tetracyclic system with 16 π-electrons, has been characterized by multinuclear NMR spectroscopy, and its structure determined by single crystal X-ray crystallography. Cyclic voltammetry studies in THF show an irreversible reduction wave at −1.73 V versus Fc+/Fc.