One-electron oxidation of an organic molecule by B(C6F 5)3; Isolation and structures of stable non-para-substituted triarylamine cation radical and bis(triarylamine) dication diradicaloid

Authors

Xin Zheng, Nanjing University
Xingyong Wang, Nanjing UniversityFollow
Yunfan Qiu, Nanjing University
Yuantao Li, Nanjing University
Chenkun Zhou, Nanjing University
Yunxia Sui, Nanjing University
Yizhi Li, Nanjing University
Jing Ma, Nanjing University
Xinping Wang, Nanjing University

RIS ID

108726

Publication Details

Zheng, X., Wang, X., Qiu, Y., Li, Y., Zhou, C., Sui, Y., Li, Y., Ma, J. & Wang, X. (2013). One-electron oxidation of an organic molecule by B(C6F 5)3; Isolation and structures of stable non-para-substituted triarylamine cation radical and bis(triarylamine) dication diradicaloid. Journal of the American Chemical Society, 135 (40), 14912-14915.

Abstract

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 32+, providing a rare example of structurally characterized bis(triarylamine) "bipolarons". 32+ can be directly prepared by the reaction of 3 with 2 equiv of Ag+. X-ray structural analysis together with theoretical calculation shows that 32+ has singlet diradical character and is analogous to Chichibabin's hydrocarbons. 2013 American Chemical Society.