Di(p-benzi)[40]decaphyrin(1.0.0.0.0.1.0.0.0.0) BF complex and tris(p-benzi)[60]pentadecaphyrin(1.0.0.0.0.1.0.0.0.0.1.0.0.0.0) BF complex were synthesized by Suzuki-Miyaura coupling of α,α'-diborylated tetrapyrrole BF -complex with 1,4-diiodobenzene. Bis-BF complex was converted to bis-Pd complex via its free base. Macrocycles bis-BF and tris-BF complex take Möbius topology but are nonaromatic, since the macrocyclic conjugation is disrupted by the locally aromatic 1,4-phenylene units. In contrast, bis-Pd complex is a weakly Hückel 38π-aromatic macrocycle as evinced by its red-shifted, enhanced, and structured Q-like bands and a small electrochemical HOMO-LUMO gap. Interestingly, one 1,4-pheylene part of bis-Pd complex takes a quinonoidal distorted structure and the other takes a usual benzene structure in a figure-eight conformation with Hückel topology.
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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).
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