Reversible Solution π-Dimerization and Long Multicenter Bonding in a Stable Phenoxyl Radical

Nico M. Bonanno, Prashanth K. Poddutoori, Kazunobu Sato, Kenji Sugisaki, Takeji Takui, Alan J. Lough, Martin T. Lemaire

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


Reversible solution π-dimerization is observed in the stable neutral phenoxyl radical 2,6-bis-(8-quinolylamino)-4-(tert-butyl)phenoxyl baqp and is spectroscopically characterized. This behavior, not previously observed for π-extended phenoxyl radicals, is relevant to the formation of long multicenter bonding in the π-dimer at low temperature akin to previously reported phenalenyl radicals. Our experimental data are supported in a quantitative manner by results from density functional theory (DFT) and ab initio molecular orbital theory calculations. Our theoretical results indicate that the solution dimer features strong bonding interactions between the two phenoxyl rings but that the stability of the dimer is also related to dispersion interactions between the flanking nearly parallel quinolyl rings.

Original languageEnglish (US)
Pages (from-to)14906-14910
Number of pages5
JournalChemistry - A European Journal
Issue number56
StatePublished - Oct 9 2018


  • density functional calculations
  • molecular devices
  • multicenter bonding
  • stable radicals
  • π-dimerization

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