Investigation of Time-Kill Evaluation and Antioxidant Activities of New Tetra-Substituted Metallophthalocyanines Bearing 4-(Trifluoromethoxy)thiophenyl Groups

In the present work, a new phthalonitrile derivative bearing 4-(trifluoromethoxy)-thiophenyl group at the 4-position (2) has been synthesized. Cyclotetramerization of 4-[4-(trifluoromethoxy)-thiophenyl] phthalonitrile (2) in appropriate high-boiling solvents gave the desired peripherally tetra-substituted zinc ({2(3),9(10),16(17),23(24)-tetrakis-[4-(trifluoromethoxy)-thiophenyl]-phthalocyaninato} zinc(II) (3)) and cobalt phthalocyanines ({2(3),9(10),16(17),23(24)-tetrakis-[4-(trifluoromethoxy)- thiophenyl]-phthalocyaninato} cobalt(II) (4)). The resulting phthalonitrile and phthalocyanine derivatives were characterized by the ¹H NMR, ¹³C NMR, ¹⁹F NMR, elemental analysis, UV-Vis, FT-IR and mass spectrometric methods. Aggregation properties of macrocycle 3 were investigated in the different concentrations and various solvents. The biological activities of the newly synthesized compounds were investigated by using well diffusion and growth curve kinetic assay. In both methods, the molecules exhibited inhibition effect only on gram negative bacteria. According to the results; molecule 4 showed the highest inhibition activity at both tested concentrations. Antioxidant activities were also evaluated by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and reducing power assays and the molecules performed moderate antioxidant activity.