Synthesis and antioxidant, aggregation, and electronic properties of 6-tert-butyl-1,4-benzodioxine substituted phthalocyanines

Abstract

As a starting material, 7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile was prepared by the reaction of 4-tert-butylcatechol with 4,5-dichlorophthalonitrile. Metallophthalocyanine complexes (4–7) were obtained by cyclotetramerization of 7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile. All compounds were characterized by elemental analysis and other spectroscopic methods (IR, UV/Vis, and 1 H NMR). Phthalocyanine compounds remained nonaggregated in tetrahydrofuran at the studied concentration ranges. Metallophthalocyanines (4–7) were tested for their antioxidant activities. The antioxidant activity processes included evaluation of radical-scavenging activity, chelating activity, and reducing power. These compounds were compared to standard antioxidant ascorbic acid. The electronic data of the new compounds were obtained by computational calculations at the B3LYP/6-31G (d,p) level of theory.