Metal-Mediated Synthesis of Antiaromatic Porphyrinoids from a BODIPY Precursor

(Figure Presented) Metallic route to antiaromaticity: The synthesis of a butadiyne-bridged cyclic BODIPY dimer (see structure; C white, B orange, N blue, F green) and trimer was achieved through Pd-catalyzed Stille coupling and Cu-mediated Glaser-type coupling. These cyclic BODIPYs were found to be stable 24π- and 36π-antiaromatic porphyrinoids with planar conformations, and their structures, electronic states, and reactivity were explored. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.