Non-peripheral tetra methoxylated pyrazoline bearing CoII, CuII and MnIIICl phthalocyanines: Syntheses, electrochemistry and spectroelectrochemistry

• Published in: Journal of organometallic chemistry 2022-08, Vol.973-974, p.122405, Article 122405
• Main Authors: Yalazan, Halise, Kantekin, Halit, Budak, Özlem, Koca, Atıf
• Format: Article
• Language: English
• Subjects: Electrochemistry; Phthalocyanines; Pyrazoline; Spectroelectrochemistry; Syntheses
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2022.122405

•Synthesis of pyrazoline containing methoxy groups.•Electrochemical properties of metallated phthalocyanines.•Spectroelectrochemical properties of metallated phthalocyanines. The novel and highly soluble cobalt(II), copper(II) and manganese(III) phthalocyanines ((Pc-Co, Pc-Cu, and Pc-Mn) bearing 3-(5-(3,5-dimethoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)phenol have been synthesized and characterized by FT-IR, NMR, UV-Vis and mass spectroscopic methods. Additionally, electrochemical and spectroelectrochemical properties of these phthalocyanine compounds were investigated. Due to the redox inactivity of the Cu2+ central cation of (Pc-Cu), Pc based reductions and oxidation processes are recorded. [CoIIPc2−]/[CoIPc2−]1− and [CoIIPc2−]/[CoIIIPc2−]1+ couples for the central metal redox reactions, and [CoIPc2−]1−/[CoIPc3−]2−, [CoIPc3−]2−/[CoIPc4−]3− and [CoIIIPc2−]1+/[CoIIIPc1−]2+ couples for the Pc based reduction and oxidation are observed respectively with (Pc-Co). Like (Pc-Co), (Pc-Mn) also illustrated metal-based reduction processes, [Cl1−-MnIIIPc2−]/[Cl1−-MnIIPc2−]1− and [Cl1−-MnIIPc2−]1−/[Cl1−-MnIPc2−]2− in addition to the Pc based [Cl1−-MnIPc2−]2−/[Cl1−-MnIPc3−]3−, [Cl1−-MnIPc3−]3− /[Cl1−-MnIPc4−]4− and [Cl1−-MnIIIPc2−]/[Cl1−-MnIIIPc1−]1+ redox couples were also recorded. These redox mechanisms were supported with the characteristic spectral changes observed during the in-situ spectroelectrochemical measurements. Especially metal-based electron transfer changes caused distinct spectral and color changes, which are the desired properties of the complexes for the possible opto-electrochemical applications. [Display omitted]