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Related Concept Videos

Redox Reactions01:24

Redox Reactions

56.6K
Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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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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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
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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Radical Formation: Addition00:47

Radical Formation: Addition

1.8K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.8K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.0K
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.
Along with electronic...
2.0K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.0K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Mapping structure-property relationships in a 6-oxo-verdazyl radical by variable pressure crystallography and density functional theory.

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Redox-Addressable Single-Molecule Junctions Incorporating a Persistent Organic Radical.

Saman Naghibi1, Sara Sangtarash2, Varshini J Kumar3

  • 1Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.

Angewandte Chemie (International Ed. in English)
|March 15, 2022
PubMed
Summary

Researchers integrated persistent radicals into molecular electronics, retaining their open-shell character at room temperature. This breakthrough enables single-molecule transistors with tunable states and electronic rectification for advanced nanodevices.

Keywords:
Molecular DevicesMolecular ElectronicsRadicals

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Area of Science:

  • Molecular electronics
  • Nanotechnology
  • Organic chemistry

Background:

  • Integrating open-shell species into nanodevices is crucial for molecular electronics.
  • Open-shell character is often lost upon contact with metallic electrodes in molecular devices.

Purpose of the Study:

  • To fabricate single-molecule devices retaining radical character at room temperature.
  • To demonstrate electrochemical gating for state control in radical-based molecular transistors.
  • To investigate electronically driven rectification in such systems.

Main Methods:

  • Fabrication of single-molecule devices using break-junction techniques.
  • Incorporation of a 6-oxo-verdazyl persistent radical.
  • Electrochemical gating in a single-molecule transistor configuration.

Main Results:

  • Retention of open-shell radical character at room temperature.
  • In situ reduction to a closed-shell anionic state via electrochemical gating.
  • Observation of electronically driven rectification due to bias-dependent resonance alignment.

Conclusions:

  • Demonstrated successful integration of persistent radicals into functional nanodevices.
  • Paved the way for studying electronic, magnetic, and thermoelectric properties of open-shell species.
  • Highlighted the potential for radical-based molecular components in transistors and rectifiers.