In this study, 3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy group substituted metal-free and metallo-phthalocyanines have been synthesized. The new compounds have been characterized by a combination of several spectroscopic techniques. Using 1,1-diphenyl-2-picrylhydrazine (DPPH), OH radical scavenging, and reducing power tests, the antioxidant properties of these phthalocyanines were assessed. CoPc showed the highest antioxidant activity for DPPH assay, ZnPc and MnPc exhibited the highest and smilar antioxidant activity at reducing power assay, ZnPc demonstrated the highest antioxidant activity at OH scavenging activity. By using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, cytotoxicity of phthalocyanines was evaluated, and iNOS mediated nitric oxide (NO) generation was carried out.