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

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...

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Published inJournal of the American Chemical Society Vol. 135; no. 40; pp. 14912 - 14915
Main Authors Zheng, Xin, Wang, Xingyong, Qiu, Yunfan, Li, Yuantao, Zhou, Chenkun, Sui, Yunxia, Li, Yizhi, Ma, Jing, Wang, Xinping
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 09.10.2013
Subjects
aluminum
cations
hydrocarbons
open reading frames
oxidation
silver
X-radiation
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Summary: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.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja407318h