Peripheral Functionalization of Antiaromatic 5,15-Dioxaporphyrin for the Synthesis of Oligomers

Partial peripheral functionalization of the antiaromatic nickel(II) 5,15-dioxaporphyrin (NiDOP) was explored to create substituted products suitable as substrates for oligomer synthesis. Syn- and anti-type diaryl-substituted NiDOPs were synthesized from tribromo-substituted dipyrrin through Suzuki-Miyaura coupling and separated by silica gel column chromatography. The unsubstituted β-positions adjacent to the meso-oxygen atoms were further used to synthesize a β, β'-linked dimer.