Synthesis and solution properties of phthalocyanines substituted with four crown ethers

Metal-free and metal phthalocyanines (M = Ni, Zn, Co) substituted with four benzo-15-crown-5 units through oxy-bridges have been synthesized from a new phthalonitrile derivative, 1-{[(benzo-15-crown-5)-4′-yl]oxy}phthalonitrile (3). The newly prepared compounds have been characterized by elemental analyses, IR, 1H NMR, MS and UV–Vis spectroscopy. Alkali metal interactions of the crown ethers on the zinc phthalocyaninato (6) are shown to form intermolecular adduct. The electrochemical properties of ZnPc were investigated by using cyclic voltammetry and controlled potential coulometry.