Reversible Reduction and Reoxidation of Thin Films of Tetrapyrazinotetraazaporphyrines

Abstract
The electrochemical properties of Cu‐tetra(pyrazino [2,3])‐[b,g,l,q]‐5,10,15,20‐tetraazaporphyrine, 4, and Cu‐tetra(5,6‐dicyanopyrazino [2,3]) [b,g,l,q]‐5,10,15,20‐tetraazaporphyrine, 5, as thin films in contact with an aqueous acid electrolyte were investigated by cyclic voltammetry. The electrodes show stable electrochromic reduction and reoxidation. A strong shift of the redox potentials into the anodic direction could be accomplished in comparison with the analogue compounds Cu‐phthalocyanine, 1, and Cu‐2,3,9,10,16,17,23,24‐octacyanophthalocyanine, 2. There is strong evidence for an irreversible structural change of 4 during the first reduction cycle.
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