Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality

The synthesis of novel metallophthalocyanines (M = Zn, Ni) bearing substituted benzyl protected 1,2,3-triazole moieties at peripheral positions is described for the first time via direct cyclotetramerization. These complexes have been characterized by a combination of FT-IR, 1H NMR, HRMS and UV–Vis spectroscopy techniques and all the new compounds are highly soluble in most common organic solvents. In addition, the electrochemical and electrochromic behaviors of the complexes are investigated. Cyclic voltammetry and differential pulse voltammetry measurements demonstrate ligand base oxidations and reductions for both the Zn(II) and Ni(II) phthalocyanines by the transfer of one electron in each electrochemical step. The redox couples are identified in situ by monitoring the electronic absorption spectral changes during the electrolysis.

Graphical abstractThe synthesis of novel metallophthalocyanines (M = Zn, Ni) bearing substituted benzyl protected 1,2,3-triazole moieties at peripheral positions is described for the first time via direct cyclotetramerization. These complexes have been characterized by a combination of FT-IR, 1H NMR, HRMS and UV–Vis spectroscopy techniques and all the new compounds are highly soluble in most common organic solvents. In addition, the electrochemical and electrochromic behaviors of the complexes are investigated. Cyclic voltammetry and differential pulse voltammetry measurements demonstrate ligand base oxidations and reductions for both the Zn(II) and Ni(II) phthalocyanines by the transfer of one electron in each electrochemical step. The redox couples are identified in situ by monitoring the electronic absorption spectral changes during the electrolysis.Figure optionsDownload full-size imageDownload as PowerPoint slide