Metallo-phthalocyanines containing triazole substituents: Synthesis, spectroscopic and photophysicochemical properties

Abstract

Magnesium(II) (4), lead(II) (5) and zinc(II) (6) phthalocyanines were prepared. The structures of 4–6 were confirmed by the spectroscopic characterization such as FT-IR, ¹H-NMR, MALDI-TOF mass, UV-vis and fluorescence spectral data. The aggregation behavior of the triazole substituted phthalocyanines (4–6) was investigated in different solvents and no aggregation was observed. The photophysicochemical properties of 4–6 were investigated in DMSO. The photophysical and photochemical behaviors varied depending on the type of metal in the center of phthalocyanine. The zinc(II) phthalocyanine 6 showed the highest singlet oxygen quantum yield and the highest photostability. The magnesium(II) phthalocyanine 4 exhibited the highest fluorescence quantum yield. The zinc(II) phthalocyanine 6 has good photosensitizer performance due to its high singlet oxygen generation ability, high photostability and formation of non-aggregated species.

Graphical Abstract

Keywords:

• Phthalocyanine
• triazole
• fluorescence
• singlet oxygen
• photosensitizer

Disclosure statement

No potential conflict of interest was reported by the authors.