Synthesis of new metal-free and metal-containing phthalocyanines with tertiary or quaternary aminoethyl substituents

A novel phthalodinitrile derivative carrying dimethylatrunoethylsulfanyl gr oups at positions 4 and 5 was synthesized from 2-dimethylaminoethanethiol h ydrochloride and 1,2-dichloro-4,5-dicyanobenzene. Its cyclotetramerization in the presence of 2-dimethylamino-ethanol or metal salts (CoCl2, Zn(OAc)(2 )) gave metal-free or metal-containing phthalocyanines (M = Co or Zn). Thes e phthalocyanines were converted into water soluble quaternized products by reaction with methyl iodide. The new compounds were characterized by eleme ntal analysis, IR, NMR, and electronic spectra.