m-Benziporphyrin(1.1.0.0) and m-pyreniporphyrin(1.1.0.0) were prepared as ring-contracted carbaporphyrins. While m-Benziporphyrin(1.1.0.0) was unstable, m-pyreniporphyrin(1.1.0.0) was fairly stable. Both of their Pd complexes showed distorted coordination structures with extremely short Pd-C bonds. As compared with the reported m-benziporphyrin Pd complexes, these Pd complexes showed considerably small HOMO-LUMO gaps, despite their smaller molecular size. Pd metalation of the m-pyreniporphyrin(1.1.0.0) dimer gave the corresponding Pd complex, which showed similar distorted coordination and a smaller HOMO-LUMO gap. Finally, Pd metalation of a pyrene-sharing formal p-benziporphyrin(1.1.1.1) dimer gave a nonaromatic Pd dimer, which rearranged to an aromatic Pd complex upon treatment with alumina.
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