One-Electron Oxidation of an Organic Molecule by B(C6F5)3; Isolation and Structures of Stable Non-para-substituted Triarylamine Cation Radical and Bis(triarylamine) Dication Diradicaloid,Journal of the American Chemical Society

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One-Electron Oxidation of an Organic Molecule by B(C6F5)3; Isolation and Structures of Stable Non-para-substituted Triarylamine Cation Radical and Bis(triarylamine) Dication Diradicaloid
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2013-09-26 , DOI: 10.1021/ja407318h
Xin Zheng ₁ , Xingyong Wang ₁ , Yunfan Qiu ₁ , Yuantao Li ₁ , Chenkun Zhou ₁ , Yunxia Sui ₁ , Yizhi Li ₁ , Jing Ma ₁ , Xinping Wang ₁

Affiliation

The methylene-bridged triphenylamine 2 has been oxidized to planar radical cation 2(•+) by B(C6F5)3 or Ag(+). Further reaction of 2(•+)[Al(ORF)4](-) and 2 with trace amounts of silver salt resulted in dication 3(2+), providing a rare example of structurally characterized bis(triarylamine) "bipolarons". 3(2+) can be directly prepared by the reaction of 3 with 2 equiv of Ag(+). X-ray structural analysis together with theoretical calculation shows that 3(2+) has singlet diradical character and is analogous to Chichibabin's hydrocarbons.

中文翻译：

B(C6F5)3 对有机分子的单电子氧化；稳定的非对位取代的三芳胺阳离子自由基和双（三芳胺）二自由基双自由基的分离和结构

亚甲基桥联的三苯胺 2 已被 B(C6F5)3 或 Ag(+) 氧化成平面自由基阳离子 2(•+)。2(•+)[Al(ORF)4](-) 和 2 与痕量银盐的进一步反应导致双阳离子 3(2+)，提供了结构表征的双（三芳基胺）“双极化子”的罕见例子。3(2+)可以通过3与2当量的Ag(+)反应直接制备。X 射线结构分析和理论计算表明 3(2+) 具有单线态双自由基特征，类似于 Chichibabin 的碳氢化合物。

更新日期：2013-09-26

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