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Updated: May 21, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Open-Shell States in Dynamic Diradicaloids
Krzysztof Dzieszkowski1, Miłosz Pawlicki1
1Department Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387, Kraków, Poland.
Abstract:
The open-shell organic and carbon-based systems, with either a doublet, triplet or higher spin-states, play a key role in contemporary research, opening potential applicability for several crucial fields. Among those derivatives, specific attention has been given to p-phenylene-based systems derived from the original Thiele hydrocarbon. These systems stabilize an open-shell diradicaloid resonance structure with a thermally accessible triplet state and are derived from a quinone-benzene (Clar's sextet) equilibrium. In our discussion, we very carefully choose examples which focus on fundamental derivatives that merge diatropic subunits, ready to stabilize two unpaired electrons via a dynamic modulation of geometry. This process provides an additional factor to the resonance energy of aromatics, mostly responsible for stabilization of two unpaired electrons.
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