Abstract

The electrochemical behavior in nonaqueous media of a series of five newly synthesized azo-stilbene dyes is investigated with the aim of elucidating the anodic oxidation mechanism of the latter to gain a better understanding of potential oxidative degradation phenomena to find new and environmentally sustainable electrochemical methods for the abatement of dyes from industrial wastewater. In addition, the frontier orbital energies of optimized conformers have been computed using quantum chemical calculations at the B3LYP-D3 (dispersion corrected Becke, 3-parameter, Lee Yang Parr) level of theory. Cyclic voltammetry experiments show that anodic oxidation of the studied chromophore structures follows an irreversible pathway and most probably occurs at the amide nitrogen. Validation of experimental results has been conducted by computation of various global reactivity descriptors, confirming that substituents grafted on the benzene ring actively influence the oxidation/reduction potentials.

Graphical abstract

中文翻译：

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一些新合成的偶氮二苯乙烯显色结构的电化学和密度泛函理论研究

摘要

研究了一系列五种新合成的偶氮二苯乙烯染料在非水介质中的电化学行为，旨在阐明后者的阳极氧化机制，以更好地了解潜在的氧化降解现象，从而找到新的且环境可持续的电化学方法减少工业废水中的染料。此外，优化构象异构体的前沿轨道能量已使用 B3LYP-D3（色散校正 Becke，3 参数，Lee Yang Parr）理论水平的量子化学计算进行了计算。循环伏安实验表明，所研究的发色团结构的阳极氧化遵循不可逆的途径，并且最有可能发生在酰胺氮处。通过计算各种全局反应性描述符对实验结果进行了验证，确认接枝在苯环上的取代基主动影响氧化/还原电位。

图形概要