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This study focuses on the synthesis, spectral, antioxidant and antibacterial properties of the metal-free, zinc and cobalt phthalocyanines (3–8) bearing 4-methoxy-phenoxy substituents on the nonperipheral [(1(4), 8(11), 15(18), 22(25)] or peripheral [2(3), 9(10), 16(17), 23(24)] positions. The new synthesized complexes 7 and 8 have been characterized by elemental analysis, FT-IR, MALDI-MS, and UV-vis spectral data. The antioxidant activities of all tested compounds were investigated by applying three different antioxidant methods such as radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl, chelating ability to ferrous ions and reducing power activity methods. In addition, the antibacterial activities of the compounds were screened by disc diffusion method against one gram-negative and four gram-positive bacteria. The tested phthalocyanine compounds showed very good antioxidant activity and promising antibacterial properties.