Photophysicochemical properties of [Tetrakis 6-(tert-butyl)-2,3-dihydrobenzo [b] [1,4] dioxine) phthalocyaninato] In(III) and Zn(II) with very high singlet oxygen quantum yield

• Published in: Inorganica Chimica Acta 2021-11, Vol.527, p.120545, Article 120545
• Main Authors: Zeki, K., Lokmacı, E., Doğu, Ezgi, Khene, S., Salih, B., Canlıca, M.
• Format: Article
• Language: English
• Subjects: 4-tert-butylcatechol; Density funcitonal theory; Density functional theory; Fluorescence; Herbivores; Indium phthalocyanine; Photodegradation; Photodynamic therapy; Singlet oxygen; Singlet oxygen quanum yield; Zinc phthalocyanine
• ISSN: 0020-1693; 1873-3255
• DOI: 10.1016/j.ica.2021.120545

[Display omitted] •New phthalocyanine complexes containing 4-tert-butyl groups were synthesized.•The photophysical and photochemical properties were described.•The complexes ZnPc and InPc show highly singlet oxygen quantum yield.•This complexes show potential for PDT of cancer as photosensitizers. Synthesis and photophysicochemical properties of [tetrakis 6-(tert-butyl)-2,3-dihydrobenzo [b] [1,4] dioxine) phthalocyaninato] In(III) (InPc-4) and [tetrakis 6-(tert-butyl)-2,3-dihydrobenzo [b] [1,4] dioxine) phthalocyaninato] Zn(II) (ZnPc-5) containing 4-tert-butylcatechol at the peripheral positions are synthesised for application as photosensitisers in photodynamic therapy (PDT). Fluorescence quantum yield, singlet oxygen quantum yield and photodegradation quantum yield were determined for each complex. High singlet oxygen quantum yield of 0.84 and 0.86 (in THF) were obtained for InPc-4 and ZnPc-5, respectively. Density functional theory (DFT) and time dependent density functional theory (TDDFT) were carried out to rationalise the experimental results.