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 oxygengeneration properties of 2-furylmethoxy substituted gallium and metal-free phthalocyanines (2 and3, respectively) are reported for the first time. Characterization of the novel synthesized compoundswas performed with elemental analysis, ultraviolet-visible spectrophotometry, fourier transforminfrared spectrometry, 1H-NMR spectroscopy and mass spectrometry. When the concentrationbehavior of the synthesized complexes is examined in a certain concentration range in THF, it hasbeen shown that the phthalocyanines predominantly consist of monomeric species. Furyl-containingnew phthalocyanines are quite soluble in common organic solvents and this makes them possible tobe used in several important applications. Fluorescence behavior of these phthalocyanines wereinvestigated. In this study, the metal ion’s effect on the UV-Vis and photophysical features of the MPcsis also cited. These results show that the metal in the core of the phthalocyanine is an important factorin the fluorescence behavior and quantum yield (ΦF) of the complexes. In singlet oxygen generationstudies showed that the phthalocyanines containing the 2-furylmethoxy group indicated a high levelof photosensitization and singlet oxygen generation capacity. Consequently, these gallium and metalfreecomplexes are promising photosensitizer for photodynamic therapy applications.