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

Abstract

The synthesis of novel, A[Formula: see text]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)-[Formula: see text]-tolyldiazenyl)phenyl)diazenyl)naphthalen-2-yl)oxy)phthalonitrile and 4-nitrophthalonitrile. The new unsymmetrical metal-free and metallophthalocyanines have been characterized using elemental analyses, [Formula: see text]H NMR, FT-IR, UV-vis and mass spectroscopic data. The aggregation properties of the compounds were investigated in a concentration range of 1.0 × 10[Formula: see text] M–6.25 × 10[Formula: see text] 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.