Synthesis and photophysical properties of a novel ethynyl zinc(II) phthalocyanine and its functionalized derivative with click chemistry

The synthesis of novel, symmetrical zinc(II) phthalocyanine (ZnPc) bearing four ethynylcyclohexyloxy terminal moieties was achieved by cyclotetramerization of novel 4-(2-ethynylcyclohexyloxy) phthalonitrile in pentanol in the presence of DBU and zinc acetate without any protective/deprotective chemistry. Subsequently, this new zinc(II) phthalocyanine derivative was reacted with 6-azido-hexanoic acid under «click-chemistry» conditions to give phthalocyanine-hexanoic acid conjugates linked by 1,2,3-triazole units. The new compounds have been characterized by using elemental analyses, UV-vis, FTIR, ¹H NMR and mass spectroscopic data. The aggregation properties of the compounds were investigated in different concentrations. General trends are also described for fluorescence quantum yields and lifetimes of novel zinc derivatives in tetrahydrofuran. The fluorescence of the tetrasubstituted zinc(II) phthalocyanine complexes is effectively quenched by 1,4-benzoquinone (BQ) in THF.