Abstract
The β-functionalization of 5,15-diazaporphyrins (DAPs) with phosphoryl, phenoxy, sulfanyl, and sulfonyl groups was achieved by either cross-coupling or aromatic nucleophilic substitution reactions of β-bromo- and β,β′-dibromo-DAPs. The heteroatom-containing functional groups at the β-positions strongly affected the redox properties of the DAP π-systems.