Control of electron-transfer reduction by protonation of zinc octabutoxyphthalocyanine assisted by intramolecular hydrogen bonding.

Facile protonation of α-octabutoxyphthalocyaninato zinc(II) (Zn(OBu)(8)Pc) occurs to afford up to tetra-protonated species stabilized by intramolecular hydrogen bonding, resulting in positive shifts of the reduction potentials of Zn(OBu)(8)PcH(n)(n+) (n = 1-4) with increasing the number of protons attached to facilitate electron-transfer reduction.