In this study, the synthesis and characterization of new substituted metallophthalocyanines are described. A new phthalonitrile, 4-(5-tert-butyl-2-hydroxyphenoxy)-5-chlorophthalonitrile (3) was prepared. New compounds were characterized by UV-Vis, IR, H-1 NMR, and elemental analysis. The aggregation behavior of the cobalt (II), magnesium (II) and copper (II) phthalocyanines were studied in tetrahydrofuran and in known concentration ranges. The antioxidant activities of compounds were evaluated. Their radical-scavenging capacity, metal chelating activity and reducing power was fully studied. The compound 3 showed 100% chelating activity as EDTA at concentration 50 mg/L. The DNA interaction of copper (II) phthalocyanine compound (6) was studied using UV/Vis titration, gel electrophoresis, cyclic voltammetry. The results indicated that compound 6 interacts with CT-DNA via intercalation binding mode.