Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds,The Journal of Organic Chemistry

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Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-11-13 , DOI: 10.1021/acs.joc.3c01793
Johann O E Sosoe ₁ , Cédric Malveau ₁ , Thierry Maris ₁ , Radu Iftimie ₁ , James D Wuest ₁

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Like hydroquinones and quinones, aromatic compounds with multiple NH₂ groups and the corresponding quinonediimines have the potential to serve as components of useful redox-active organic materials. Benzene-1,2,4,5-tetramine (BTA) and its oxidized form BTA-H₂ offer a promising redox pair of this type, and the compounds have proven to be useful in many areas of chemistry. However, key aspects of their behavior have remained poorly studied, such as the nature of their protonated forms, their preferred molecular structures, their reactivity, and their organization in condensed phases. In the present work, we have used a combination of improved methods of synthesis, computation, spectroscopic studies, and structural analyses to develop a deeper understanding of BTA, BTA-H₂, their salts, and related compounds. The new knowledge is expected to accelerate exploitation of the compounds in areas of materials science where desirable properties can only be attained by properly controlling the organization of molecular components.

中文翻译：

刷新鲁道夫·尼茨基的遗产：苯-1,2,4,5-四胺及相关化合物

与氢醌和醌一样，具有多个NH ₂基团的芳香族化合物和相应的醌二亚胺具有作为有用的氧化还原活性有机材料的组分的潜力。苯-1,2,4,5-四胺 (BTA) 及其氧化形式 BTA-H ₂提供了这种类型的有前途的氧化还原对，并且这些化合物已被证明在许多化学领域中有用。然而，它们行为的关键方面仍然缺乏研究，例如它们的质子化形式的性质、它们优选的分子结构、它们的反应性以及它们在凝聚相中的组织。在目前的工作中，我们结合使用了改进的合成、计算、光谱研究和结构分析方法，以加深对 BTA、BTA-H ₂、其盐和相关化合物的了解。新知识预计将加速材料科学领域化合物的开发，在材料科学领域，只有通过正确控制分子成分的组织才能获得所需的性能。

更新日期：2023-11-13

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