Synthesis, characterization, photophysical and photochemical properties of peripherally tetra benzodioxane substituted metal-free phthalocyanine and its zinc(II) and magnesium(II) derivatives

The phthalonitrile (3) including 2-(methoxymethyl)-2,3-dihydro-1,4-benzodioxane substituent and peripherally tetra substituted metal-free (4), zinc(II) (5) and magnesium(II) (6) phthalocyanines were synthesized. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of phthalocyanines (4-6) were examined in DMSO solutions. The zinc(II) phthalocyanine (5) showed higher singlet oxygen quantum yield (Phi(Delta)=0.82) compared to metal-free (4) (Phi(Delta)=0.13) and magnesium(II) (5) (Phi(Delta)=0.29) phthalocyanine. Also, the fluorescence quenching behaviors of phthalocyanines (4-6) by 1,4-benzoquinone (BQ) were investigated. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

In this study, phthalocyanines with different substituents were synthesized and their photophysical and photochemical properties were investigated in DMSO solutions. Zinc(II) phthalocyanine showed higher singlet oxygen quantum yield compared to metal-free and magnesium(II) phthalocyanine. Additionally, the fluorescence quenching behaviors of phthalocyanines by 1,4-benzoquinone were studied.