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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.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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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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Radical Reactivity: Overview01:11

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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: Electrophilic Radicals

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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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Updated: Dec 28, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Engineering stable radicals using photochromic triggers.

Xuanying Chen1,2, Wandong Zhao2, Gleb Baryshnikov3

  • 1State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai, 200438, China.

Nature Communications
|February 20, 2020
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Summary
This summary is machine-generated.

Researchers developed a novel photochromic system for stable radical generation using light. This breakthrough enables efficient detection of peroxides, offering a faster alternative to traditional methods.

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Area of Science:

  • Organic chemistry
  • Materials science
  • Photochemistry

Background:

  • Long-lived radical species are crucial in organic chemistry and materials science.
  • Generating and stabilizing radicals using light presents significant structural challenges.

Purpose of the Study:

  • To develop a photochromic system for simultaneous photoproduction and stabilization of radical species.
  • To create a radical system applicable for sensitive and quantitative peroxide detection.

Main Methods:

  • Design and synthesis of a pyrrole and chloride assisted photochromic structure.
  • Photochemical processing in chloroform.
  • Theoretical studies and mechanism construction.
  • Application of the radical system for peroxide detection.

Main Results:

  • Simultaneous production and stabilization of a radical species via a photochemical process.
  • The designed π-system demonstrated significant spin-delocalization and steric effects, ensuring radical stability for hours, even in oxygen-saturated conditions.
  • The radical system successfully detected peroxides (e.g., TEMPO, H2O2, ozone) visually and quantitatively.
  • Achieved higher sensing rates for peroxide detection compared to conventional redox techniques.

Conclusions:

  • The developed photochromic system effectively addresses the challenge of light-induced radical generation and stabilization.
  • The system offers a novel, efficient, and rapid method for peroxide detection, with potential applications in various analytical fields.