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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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Radical Reactivity: Nucleophilic Radicals01:16

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Open-Shell States in Dynamic Diradicaloids.

Krzysztof Dzieszkowski1, Miłosz Pawlicki1

  • 1Department Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387, Kraków, Poland.

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Open-shell organic systems with multiple spin states are key in research. This study focuses on p-phenylene derivatives that stabilize unpaired electrons through geometric modulation and resonance energy.

Keywords:
Chichibabin hydrocarbonDiradicalsDynamic hydrocarbonsPhenylenesStable radicals

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Quantum Chemistry

Background:

  • Open-shell organic systems, including doublet, triplet, and higher spin states, are crucial in modern research.
  • p-Phenylene derivatives, originating from Thiele hydrocarbon, are of particular interest due to their unique electronic properties.
  • These systems exhibit a diradicaloid resonance structure with a thermally accessible triplet state, stemming from a quinone-benzene (Clar's sextet) equilibrium.

Purpose of the Study:

  • To investigate fundamental p-phenylene derivatives that stabilize open-shell diradicaloid structures.
  • To explore how the dynamic modulation of geometry contributes to stabilizing unpaired electrons.
  • To understand the role of resonance energy in stabilizing these spin states.

Main Methods:

  • Focus on fundamental derivatives merging diatropic subunits.
  • Analysis of systems capable of stabilizing two unpaired electrons.
  • Investigation of dynamic geometric modulation effects.

Main Results:

  • Demonstrated stabilization of two unpaired electrons in selected p-phenylene systems.
  • Identified the contribution of geometric modulation to electronic stabilization.
  • Highlighted the role of resonance energy in stabilizing higher spin states.

Conclusions:

  • p-Phenylene derivatives offer a promising platform for developing novel open-shell organic materials.
  • Geometric modulation is a key factor in controlling the spin states of these systems.
  • The study provides fundamental insights into the electronic stabilization of open-shell diradicaloids.