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4-[(4′-(Tert-butyl)phenoxy)phenoxy]phthalonitrile 1 has been prepared by the reaction of 4-(4-nitrophenoxy)phthalonitrile with 4-tertiarylbutylphenole. 4-((4′-tert-butyl)phenoxy)phenoxy tetrasubstituted metal-free 2, zinc(II) 3 and cobalt(II) 4 phthalocyanines have been prepared by tetramerization of compound 1. The synthesized phthalocyanines showed high solubility in common organic solvents such as CHCl[Formula: see text]. All compounds were characterized by elemental analysis and [Formula: see text]H-NMR, [Formula: see text]C-NMR, UV-vis, IR spectra. Aggregation behaviors of these compounds have been investigated in different solvents (CHCl[Formula: see text], THF, DMF and DMSO) and different concentrations in CHCl[Formula: see text]. The in vitro antioxidant activities of phthalocyanine compounds 2, 3 and 4 were evaluated in a series of assays involving DPPH radicals, hydroxyl radicals, superoxide radicals, singlet oxygen and hydrogen peroxide. Antioxidant activity of compound 2was found to be higher than that of compounds 3 and 4.