Synthesis, characterization, solution and antioxidant properties of novel tetrakis{4-[N-((3-dimethylamino)propyl)amide]phenoxy}nickel (II) phthalocyanine and its water soluble derivatives

Abstract

Zwitter ionic macro molecules can be prepared to provide functional materials applicable in various different fields such as catalysis, cleaning industry, textile industry, cosmetics and drugs with the enhanced solubility both in organic solvent and aqueous media. Tetra {4-[N-((3-dimethylamino)propyl)amide]phenoxy} substituted nickel (II) phthalocyanine (2) and its sulfobetaine, betaine, and N-Oxide derivatives (3–5) were synthesized as novel species. All newly synthesized compounds (1–5) were characterized by the combination of spectroscopic techniques such as UV–Vis, FT-IR, 1H NMR, 13C NMR, mass and elemental analysis, as well. The ionic phthalocyanine derivatives (3–5) showed excellent solubility in aqueous media due to their ionic characters. In this study, antioxidant capacities of the phthalonitrile (1) and phthalocyanines (2–5) were tested via radical scavenging methods; 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH) scavenging, 2,2′-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, and cupric reducing antioxidant capacity (CUPRAC) method. In addition to this radical scavenging studies, reducing power activity of compounds (1–5) were tested as well. Surfactant properties of ionic derivatives (3–5) were also investigated in water. Results revealed that all the synthesized compounds have antioxidant activity (1–5) and water soluble phthalocyanines (3–5) have good surfactant properties, as well.