Through-Space (Cofacial) π-Delocalization among Multiple Aromatic Centers: Toroidal Conjugation in Hexaphenylbenzene-like Radical Cations


  • We thank I. S. Neretin for computational assistance and the R. A. Welch Foundation for financial support.


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Pi and doughnuts: Highly effective through-space conjugation among cofacial (aromatic) redox centers is established in stable hexaanilinylbenzene radical cations (1.+; π conjugation shown by toroid). The radical cations show unusual intervalence absorption bands and are quantitatively analyzed by Mulliken–Hush formulation.