Synthesis, characterization and aggregation and fluorescence properties of novel highly soluble zinc phthalocyanines bearing tetrakis-4-(3-(piperidin-1-yl)phenoxy) with tetra and dodecachloro substituents

The synthesis of two new phthalocyanine precursors 4-(3-(piperidin-1-yl)phenoxy) with mono (2) and trichloro (3) substituents were carried out in this work. Cyclotetramerization of these precursors with zinc acetate gave novel tetrakis-4-(3-(piperidin-1-yl)phenoxy) with tetra (4) and dodecachloro (5) substituted zinc phthalocyanines. The synthesized new compounds were characterized using FT-IR, 1H NMR, electronic absorption spectroscopy, mass spectra and elemental analysis. The aggregation behavior of zinc phthalocyanines 4 and 5 was investigated in different concentrations of dichloromethane (DCM). Zinc phthalocyanines 4 and 5 showed good solubility in different organic solvents such as DCM, CHCl3, THF, benzene and toluene. Further, the aggregation behavior of zinc phthalocyanines 4 and 5 was studied before and after the addition of Triton X100. Further, the fluorescence quantum yields of zinc phthalocyanines 4 and 5 were calculated in the presence and absence of Triton X100.