Ni(II) 10-Phosphacorrole: A Porphyrin Analogue Containing Phosphorus at the Meso Position

Ni­(II) 10-Phosphacorrole, a porphyrinoid containing phosphorus at the meso position, was synthesized from a bis­(α,α′-dibromodipyrrin) Ni­(II) complex and a phosphine anion via the palladium-catalyzed formation of a C–C and two C–P bonds. The optoelectronic properties of Ni­(II) 10-phosphacorrole can be modulated effectively by oxidation or coordination of a metal to the phosphorus center. While Ni­(II) 10-phosphacorrole exhibits a distinctly aromatic character due to the cyclic conjugation of 18 π-electrons, its oxide exhibited weak antiaromaticity, which was confirmed experimentally and theoretically.