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Related Concept Videos

Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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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.
Along with electronic...
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Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
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...
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π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

4.4K
Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
4.4K
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

5.3K
An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
5.3K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
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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Related Experiment Video

Updated: Jan 10, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Robust π-conjugated radical cations.

Shilong Su1, Qian Miao1,2

  • 1Department of Chemistry, The Chinese University of Hong Kong Shatin New Territories Hong Kong China miaoqian@cuhk.edu.hk.

Chemical Science
|November 28, 2025
PubMed
Summary
This summary is machine-generated.

Robust π-conjugated radical cations are now isolable and characterized, advancing organic electronics. Stabilization strategies enhance their properties for improved material stability and device performance in p-type semiconductors.

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Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization
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Area of Science:

  • Materials Science
  • Organic Electronics
  • Chemistry

Background:

  • π-Conjugated radical cations are essential charge carriers in p-type organic semiconductors.
  • Traditionally, these open-shell, positively charged species were considered too reactive for isolation under ambient conditions.
  • Recent breakthroughs in stabilization techniques have overcome these challenges.

Purpose of the Study:

  • To provide a comprehensive review of fully characterized π-conjugated radical cations.
  • To emphasize species identified via single-crystal X-ray crystallography in the last two decades.
  • To explore structure-property relationships for applications in organic electronics.

Main Methods:

  • Review of literature focusing on π-conjugated radical cations characterized in the last 20 years.
  • Emphasis on single-crystal X-ray crystallography data.
  • Analysis of electronic and steric stabilization strategies.

Main Results:

  • Identification of key structural features and stabilization methods enabling ambient stability.
  • Demonstration of structure-property relationships crucial for organic electronic materials.
  • Evidence of enhanced material stability and potential for improved device performance.

Conclusions:

  • Robust π-conjugated radical cations can be isolated and characterized, challenging previous notions of their reactivity.
  • Understanding stabilization strategies and structure-property relationships is vital for advancing organic electronics.
  • This field holds significant promise for developing more stable and efficient organic electronic materials.