Metallo Phthalocyanines Bearing (2-((2 (p-Tolyl)amino)ethoxy) and (2-((2 (p-Tolyl)amino)ethoxy)phthalonitrile Substituents: Synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity

Abstract

The novel phthalonitrile derivatives bearing (2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy) and (2-((2-phenoxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile substituents at peripheral position were prepared by a nucleophilic displacement reaction. Cyclotetramerization of these phthalonitrile derivatives in the presence of corresponding metal salts gave the new metallophthalocyanines. The novel compounds were characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-6) M in tetrahydrofuran. In vitro three antioxidant test methods, namely diphenylpicrylhydrazyl radical scavenging activity, metal chelating activity and reducing power were used to determine the antioxidant activity of compounds. Compounds were analyzed for their antibacterial activity against some bacteria by using the disk-diffusion method. (C) 2014 Elsevier B.V. All rights reserved.