Preparation and investigation of aggregation, fluorescence and singlet oxygen generation properties of gallium and metal-free phthalocyanines

Abstract

The synthesis, characterization, aggregation, optical, fluorescence and singlet oxygen generation properties of 2-furylmethoxy substituted gallium and metal-free phthalocyanines (2 and 3, respectively) are reported for the first time. Characterization of the novel synthesized compounds was performed with elemental analysis, ultraviolet-visible spectrophotometry, fourier transform infrared spectrometry,1 H-NMR spectroscopy and mass spectrometry. When the concentration behavior of the synthesized complexes is examined in a certain concentration range in THF, it has been shown that the phthalocyanines predominantly consist of monomeric species. Furyl-containing new phthalocyanines are quite soluble in common organic solvents and this makes them possible to be used in several important applications. Fluorescence behavior of these phthalocyanines were investigated. In this study, the metal ion’s effect on the UV-Vis and photophysical features of the MPcs is also cited. These results show that the metal in the core of the phthalocyanine is an important factor in the fluorescence behavior and quantum yield (ΦF) of the complexes. In singlet oxygen generation studies showed that the phthalocyanines containing the 2-furylmethoxy group indicated a high level of photosensitization and singlet oxygen generation capacity. Consequently, these gallium and metal-free complexes are promising photosensitizer for photodynamic therapy applications.