Sub--benziporphyrin: a subcarbaporphyrinoid and its B complex with an unprecedented planar tridentate 14π-aromatic network.

Sub--benziporphyrins were synthesized by Pd-catalyzed cross-coupling of ,'-diboryl--benzitripyrrane with 9,10-bis(1,1-dibromomethylenyl)anthracene. Reaction of sub--benziporphyrin with PhBCl and triethylamine gave its B-phenyl complex as a tetracoordinate nonaromatic B complex. In contrast, the reaction with BBr and triethylamine furnished a neutral B porphyrinoid with a planar and triangular coordination as the first example, in which the -phenylene unit was partially reduced, allowing for the global 14π-aromatic circuit.

The unprecedented strong paratropic ring current of a bis-Pd complex of 5,10,23-trimesityl [28]heptaphyrin(1.1.0.0.1.0.0).

Acid-catalyzed Friedel-Crafts-type cyclization of tetrapyrrolic BF complex 1 and α,α'-dibromotripyrrin 2 gave 5,10,23-trimesityl [28]heptaphyrin(1.1.0.

Synthesis of Ni porphyrin-Ni 5,15-diazaporphyrin hybrid tapes.

Ni porphyrin (P) and Ni 5,15-diazaporphyrin (DAP) hybrid tapes were synthesized by Suzuki-Miyaura cross-coupling reactions of - or β-borylated P with β-brominated DAP followed by intramolecular oxidative fusion reactions. -β doubly linked hybrid tapes were synthesized by oxidation of singly linked precursors with DDQ-FeCl. Synthesis of triply linked hybrid tapes was achieved by oxidation with DDQ-FeCl-AgOTf with suppression of peripheral β-chlorination.