Novel phthalocyanines bearing fluoro-methylquinolin substituents: Synthesis, characterization, photophysical and photochemical properties

• Published in: Journal of organometallic chemistry 2024-12, Vol.1022, p.123421, Article 123421
• Main Authors: Demirbaş, Ümit, Özçifçi, Zehra, Akçay, Hakkı Türker
• Format: Article
• Language: English
• Subjects: Fluorescence; Photosensitizer; Photostability; Phthalocyanine; Singlet oxygen
• ISSN: 0022-328X
• DOI: 10.1016/j.jorganchem.2024.123421

•4-((6-fluoro-2-methylquinolin-4-yl)oxy)phthalonitrile.•Synthesis of peripherally tetra 4-((6-fluoro-2-methylquinolin-4-yl)oxy) substituted zinc(II) phthalocyanines and their water-soluble derivatives.•Investigation of photophysical and photochemical properties zinc(II) phthalocyanines and their water-soluble derivatives. The novel 4-((6-fluoro-2-methylquinolin-4-yl)oxy)phthalonitrile (3a), 3-((6-fluoro-2-methylquinolin-4-yl)oxy)phthalonitrile (3b), tetra 6-fluoro-2-methylquinolin-4-yl)oxy substituted zinc(II) phthalocyanines (4a and 4b) and their water soluble derivatives (5a and 5b) were prepared. The proposed structures of novel compounds were comfirmed via FT-IR, 1HNMR , UV–Vis and MALDI-TOF mass data. The aggregation tendency, fluorescence quantum yield, singlet oxygen quantum yield and photodegradation measurements were performed to examine the photodynamic therapy potential of both peripherally tetra substituted zinc(II) phthalocyanines (4a and 4b) and the water soluble quaternized tetra substituted zinc(II) phthalocyanines (5a and 5b). The result showed that both the novel tetra 6-fluoro-2-methylquinolin-4-yl)oxy substituted zinc(II) phthalocyanines (4a and 4b) and their water soluble derivatives (5a and 5b) could be used as photosensitizer agents in PDT thanks to their lack of aggregation tendency, having sufficient fluorescence emission for monitoring and produce high amount of singlet oxygen to destroy cancerous tissues and having moderate photostability. [Display omitted]