Synthesis, photophysical and electrochemical properties of novel unsymmetrical phthalocyanines with a Sudan IV moiety


Özçeşmeci İ. , Buyuk P., Nar I. , Gül A.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.22, pp.112-120, 2018 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22
  • Publication Date: 2018
  • Doi Number: 10.1142/s1088424618500177
  • Title of Journal : JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Page Numbers: pp.112-120

Abstract

The synthesis of novel, A(3)B type unsymmetrical metal-free and metallophthalocyanines bearing one aza dye group Sudan IV and three nitro terminal moieties was achieved by cyclotetramerization of novel 4-((1-((E)-(2-methyl-4-((E)-o-tolyldiazenyl)phenyl)diazenyl)naphthalen-2-yl)oxy) phthalonitrile and 4-nitrophthalonitrile. The new unsymmetrical metal-free and metallophthalocyanines have been characterized using elemental analyses, H-1 NMR, FT-IR, UV-vis and mass spectroscopic data. The aggregation properties of the compounds were investigated in a concentration range of 1.0 x 10(-4) M-6.25 x 10(-6) M. General trends were also studied for fluorescence quantum yields and lifetimes of these phthalocyanine compounds in tetrahydrofuran. The fluorescence of the synthesized unsymmetrical metal-free and metallophthalocyanines is effectively quenched by 1,4-benzoquinone (BQ) in THF. In-depth investigation of the electrochemical properties showed that nitro groups extended the reduction potentials.