One-Electron Oxidation of an Organic Molecule by B(C6F5)3; Isolation and Structures of Stable Non-para-substituted Triarylamine Cation Radical and Bis(triarylam
The methylene-bridged triphenylamine 2 has been oxidized to planar radical cation 2鈥? by B(C6F5)3 or Ag+. Further reaction of 2鈥?[Al(ORF)4]鈭?/sup> and 2 with trace amounts of silver salt resulted in dication 32+, providing a rare example of structurally characterized bis(triarylamine) 鈥渂ipolarons鈥? 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鈥檚 hydrocarbons.