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Synthesis, characterization, aggregation, fluorescence and antioxidant properties of bearing (4-(methylthio)phenylthio) tetra substituted phthalocyanines

2017    Aydin, Melike; Alici, Esma Hande; Bilgicli, Ahmet T.; Yarasir, M. Nilufer; Arabaci, Gulnur

A new substituted phthalonitrile derivative, 4-(4-(methylthio)phenylthio) phthalonitrile was prepared by nucleophilic displacement reaction between 4-(methylthio)phenylthio and 4-nitrophthalonitrile. Tetra phthalocyanines [M: 2H(2), Zn(II)(3), Co(II)(4)] with four peripheral 4-(methylthio)phenylthio groups were synthesized by cyclotetramerization. They were characterized by elemental analysis, FTIR, H-1 NMR, C-13 NMR, MALDI-TOF, UV-vis, Fluorescence, AFM, and spectral data. Their aggregation properties were examined in THF by UV-vis and Fluorescence spectrophotometers. The antioxidant properties of newly synthesized metal-free and metallophthalocyanines were also investigated by using three different antioxidant methods: free radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH), ferrous ion chelating ability and reducing power activity. The highest DPPH activity was found from cobalt phthalocyanines (4) compound respectively. All tested phthalocyanines compounds had fairly ferrous ion chelating activity and showed very good reducing power. They had even better reducing power than the standards antioxidant compounds such as ascorbic acid and BHT. Thus, Tetra phthalocyanines [M: 2H (2), Zn(II)(3), Co(II)(4)] with four peripheral 4-(methylthio)phenylthio groups could be used as potential antioxidant compounds. (C) 2017 Elsevier B.V. All rights reserved.