Novel phthalocyanines bearing both quaternizable and bulky substituents

A new phthalonitrile derivative bearing dimethylaminoethylsulfanyl- and diethoxymalonyl-substituents at peripheral positions has been synthesized. Cyclotetramerization of this dinitrile in hexanol gave the desired cobalt(II) and zinc(II) phthalocyanines (4 and 5) with dimethylaminoethylsulfanyl and dihexoxymalonyl groups on periphery. Four dimethylaminoethyl groups of the former were quaternized to yield a water-soluble cobalt(II) phthalocyanine. Electrochemical redox properties of these phthalocyanines were investigated by cyclic voltammetry and applied chronocoulometry techniques.