Newly synthesized zinc phthalocyanine bearing sixteen quaternized imidazolyl moieties on the periphery displays high water-solubility, lack of aggregation and high singlet oxygen quantum yield in water (ΦΔ > 0.33). The in vitro tests indicated excellent anticancer photodynamic activity (EC50 = 36.7 nM) and low dark toxicity to non-cancerous cells (TC50 = 395 μM).

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Two series of peripherally substituted azaphthalocyanines (AzaPcs) containing different transition metals ( Al(III), Zn(II), Ga(III), In(III) and Fe(II) ) were synthesized and studied for their photophysical properties. As confirmed by UV-vis and1H NMR analyses, the non-aggregation behavior was effectively induced by the applied bulky peripheral substituents which had no effect on the photophysical properties. Tuning the Q-band position was clearly achievable by using different central heavy metals which have considerable effects on the fluorescence quantum yield and singlet oxygen generation efficiency. This comparative study showed an interesting linear relationship between the former and atomic number of the central metal. The indium containing complexes exhibited the best result due to the heavy metal effect and therefore could be promoted as a potential photosensitizer in photodynamic therapy (PDT) application.

This work reports on the synthesis of novel metal free, zinc, aluminum, gallium and indium tetra and octa (2,6-di-iso-propylphenoxy)-substituted phthalocyanine derivatives. UV-visible and 1H NMR analyses confirm that a non-planar conformation, adapted by the phenoxy substituents due to steric interaction in both derivative series, perfectly discourage cofacial aggregation. Fluorescence quantum yields vary as a function of the number of substituents on the ring periphery, while the fluorescence lifetimes display no distinct trend. Triplet quantum yields are significantly larger for the tetra 2,6-di-iso-propylphenoxy- substituted derivatives relative to their corresponding octa-substituted species. However there was no overall trend in the triplet lifetime values. For almost all of the phthalocyanine derivatives, singlet oxygen was produced with relatively good quantum yields. This study explores the possibility of fine-tuning their physicochemical properties by simple structural modification.

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