In this study, novel beta and alpha tetra-[4-oxy-3-methoxybenzoic acid]-substituted Co(II), Zn(II) and Cu(II) phthalocyanines were prepared by the cyclotetramerization of the new phthalonitriles (1)/(2) and the corresponding divalent metal salts. The compounds were characterized by spectral data (IR, UV–Vis, 1 H NMR and mass spectroscopies) as well as elemental analysis. These metallophthalocyanines showed excellent solubility in most organic solvents. The reduction and oxidation behaviour of the alpha- and beta-substituted complexes were established by voltammetry and in situ spectroelectrochemistry. The complexes were observed to display metal- and/or phthalocyanine ring-based redox processes. The redox and aggregation behaviours of the phthalocyanine complexes were found to be affected considerably by the nature of the substitution.