Pancake Bond Orders of a Series of π-Stacked Triangulene Radicals.

Abstract

Conjugated radicals are capable of forming π-stacking "pancake-bonded" dimers. Members of the family of triangulene hydrocarbons, non-Kekulé neutral multiradicals, can utilize more than one singly occupied molecular orbital (SOMO) to form multiple pancake-bonded dimers with formal bond orders of up to five. The resulting dimer binding energies can be quite high and the intermolecular contacts rather small compared to the respective van der Waals values. The preferred configurations are driven by the large stabilization energy of overlapping SOMOs.