Metallo and metal free phthalocyanines bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents: Synthesis, characterization, aggregation behavior, electronic, antioxidant and antibacterial properties


Ağırtaş M. S. , GUVEN M. E. , Gümüş S. , Ozdemir S., Dundar A.

SYNTHETIC METALS, vol.195, pp.177-184, 2014 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 195
  • Publication Date: 2014
  • Doi Number: 10.1016/j.synthmet.2014.06.004
  • Title of Journal : SYNTHETIC METALS
  • Page Numbers: pp.177-184

Abstract

As starting material the phthalonitrile derivative bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile derivative in the presence of corresponding metal salts gave the new metallophthalocyanines. Metal free phthalocyanine was obtained from the reaction of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile units. The novel compounds have been characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-5) M in tetrahydrofuran. The antioxidant activities of novel compounds were analyzed through radical scavenging ability of 1,1-dipheny1-2-picrylhydrazyl, chelating ability to ferrous ions and reducing power. In addition to these, the antibacterial activities of compounds were investigated. Moreover, the ground-state geometries of the complexes were optimized using B3LYP/6-31G(d,p) level of density functional theory in order to predict the three-dimensional geometries and electronic structure. (C) 2014 Elsevier B.V. All rights reserved.