Doubly and quadruply quinoline-fused porphyrins were effectively synthesized through a reaction sequence consisting of Suzuki–Miyaura coupling of β-borylated porphyrins with 2-iodoaniline and subsequent Pictet–Spengler cyclization. These quinoline-fused porphyrins display red-shifted absorption bands and higher electron-accepting abilities. This synthetic protocol also allowed the synthesis of phenanthroline-fused porphyrin dimers, which bound either a NiIIor ZnIIcation. The resultant metal complexes displayed further red shifted absorption spectra and molecular twists to effect an almost perpendicular arrangement of the two porphyrins.
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