Synthesis of anthraquinone-based azo-metal(II) complexes as potent anti-oxidizing agents

Abstract

The 3-diethylaminophenol (3-DEAP) incorporated anthraquinone mono-azo dye derivative [(E)-1-((4-(diethylamino)-2-hydroxyphenyl)diazenyl)anthracene-9,10-dione] DAAD was synthesized through an electrophilic substitution reaction. The interaction between the -OH functional group and the nitrogen atom of the azo moiety may result in intramolecular proton transfer in the DAAD. DAAD was treated with metal ions such as Co(II), Ni(II), and Cu(II) acetates in a ratio of 2 : 1 revealing an octahedral structure. Many analytical and spectroscopic methods, including UV-vis, FT-IR, (1H and 13C) NMR, HRMS, TGA, VSM, ESR, and powder XRD methods, were used to verify the structural characteristics of the compounds. Additionally, the potency of the in-vitro antioxidant properties of the ligand and its Cu(II), Ni(II), and Co(II) complexes were evaluated; the results revealed that the Co(II) complex showed a maximum percent inhibition of 85 μM against the standard ascorbic acid.