Synthesis and fluorescence properties of phthalocyanines with dibromo- and tribromo-phenoxy functionalities

The synthesis and characterization of new peripherally tetra-substituted metal-free and zinc(II) phthalocyanines with 3,4-dibromophenoxy and 2,4,5-tribromophenoxy functionalities are described for the first time in this study. Novel phthalocyanines were characterized with elemental analyses, mass, proton nuclear magnetic resonance (¹H NMR), Fourier transform infrared spectroscopy (FT-IR) and ultraviolet-visible spectroscopy (UV-vis) techniques. Aggregation properties of these compounds were investigated in the concentration range of 1-10 μM in dichloromethane before and after addition of surfactant Triton X-100. The influence of the substituent on the phthalocyanine framework, central metal ion (metal-free or zinc) and the position of the bromine group on the spectroscopic properties are also investigated.