Amino-functionalized water-soluble zinc phthalocyanines: Synthesis, photophysical, photochemical and protein binding properties

•We synthesized and characterized the aminofunctionalized zinc (II) phthalocyanines.•The photophysical and photochemical properties of these compounds were investigated in DMSO and water for comparison of solvent effect.•The effect of the phthalocyanine molecules’ symmetry on these properties was also revealed.•The fluorescence quenching properties of these compounds by addition of 1,4-benzoquinone were described in DMSO.•The binding study of these phthalocyanines to bovine serum albumin was also examined in this study.

Tetra-peripherally substituted symmetrical and low symmetrical Zn (II) phthalocyanines containing 2-[2-(2-ethoxyethoxy)ethoxy]-1-[2-((2-ethoxyethoxy)-ethoxy)ethoxymethyl] ethyloxy and [2-(tert-butoxycarbonyl)amino]ethoxy groups, as well as their deprotected amino-functionalized derivatives were synthesized for the first time. These novel zinc phthalocyanines were characterized by elemental analysis and spectroscopic methods including FT-IR, 1H and 13C NMR, MALDI-TOF, UV–vis. Their photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties were investigated in DMSO, in water and in water + triton X-100 solutions for comparison of solvents and aggregation effects. Effects of symmetries of the phthalocyanine molecules on these properties were also revealed. The fluorescence quenching of these Zn (II) phthalocyanines upon addition of 1,4-benzoquinone were examined in DMSO. Binding study of these phthalocyanine photosensitizers to bovine serum albumin one of the blood carrier proteins, was also examined in this study.

Graphical abstractIn this study, the tetra-peripherally substituted zinc (II) phthalocyanines containing amino-functionalized groups were prepared. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties of these newly synthesized compounds were investigated in DMSO and water for comparison of solvent effect. The fluorescence quenching properties of these new zinc (II) phthalocyanines by addition of 1,4-benzoquinone were described in DMSO. The binding study of these phthalocyanine photosensitizers to bovine serum albumin which is one of the blood proteins was also examined in this study.Figure optionsDownload full-size imageDownload as PowerPoint slide