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 reac- tion 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, chelat- ing 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.