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Related Concept Videos

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 Reactivity: Overview01:11

Radical Reactivity: Overview

2.8K
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 Formation: Overview01:03

Radical Formation: Overview

2.7K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
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Radical Formation: Addition00:47

Radical Formation: Addition

2.3K
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...
2.3K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.5K
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.
4.5K
Radical Autoxidation01:20

Radical Autoxidation

3.3K
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Related Experiment Video

Updated: Feb 18, 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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Air-Stable and Photo-Induced Organic Radicals by Parallel Molecular Stacking in Crystal Network.

Jianye Yang1, Peijuan Zhang1, Qifei Shen1

  • 1School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Xi'an Key Laboratory of Sustainable Polymer Materials, Xi'an Jiaotong University, Xi'an, P. R. China.

Advanced Healthcare Materials
|February 17, 2026
PubMed
Summary

Researchers developed stable, photo-induced organic radicals using triarylamine derivatives. Compound 1 demonstrated rapid radical generation and enhanced near-infrared properties, showing potential for phototheranostics.

Keywords:
fluorescence imagingorganic radicalsparallel stackingphotodynamic/photothermal therapyreactive oxygen species

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Organic radicals are crucial but challenging to stabilize, especially under photo-induction.
  • Developing air-stable and photo-responsive radicals is essential for advanced applications.

Purpose of the Study:

  • To design and synthesize triarylamine derivatives for tunable molecular stacking and radical stabilization.
  • To investigate the photo-induced electron transfer and radical generation capabilities of these compounds.
  • To explore the potential of these radicals in phototheranostics.

Main Methods:

  • Synthesis of a series of triarylamine derivatives (compounds 1-6).
  • Crystallographic analysis to study molecular stacking and hydrogen-bonding networks.
  • Photophysical characterization including UV-Vis absorption, emission spectroscopy, and radical generation studies.
  • Preparation of radical-based nanoparticles via nanoprecipitation.

Main Results:

  • Compound 1 exhibited a robust 2D hydrogen-bonded crystal network facilitating inter-molecular electronic transfer.
  • Rapid photo-induced radical generation in compound 1 (5-min saturation) with significant enhancement in near-infrared absorption (22.5-fold) and emission (8-fold).
  • Stable radical signals detected in solid-state crystals for over a month; efficient NIR fluorescence, reactive oxygen species generation, and heat production under irradiation.

Conclusions:

  • The designed triarylamine derivative (Compound 1) demonstrates excellent photo-induced radical generation and stability.
  • Its unique crystal network enhances electronic properties, enabling rapid photo-response.
  • The developed radical-based nanoparticles show promise for simultaneous fluorescence imaging and phototherapy (phototheranostics).