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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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 molecule. These three...
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...
Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
Radical Formation: Overview01:03

Radical Formation: Overview

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 latter, also known...
Radical Formation: Addition00:47

Radical Formation: Addition

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 unpaired...

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Updated: May 15, 2026

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

Published on: April 19, 2019

π-Radical Cascades to Peri-Fused Triangulene Dimers.

Paula L Widmer1, Leoš Valenta1, Maximilian Mayländer2

  • 1Department of Chemistry, University of Zurich, Zurich, Switzerland.

Angewandte Chemie (International Ed. in English)
|May 14, 2026
PubMed
Summary

Researchers controlled the reactivity of open-shell molecular graphene fragments. Steric bulk guided reactions, enabling selective formation of graphene nanostructures through controlled π-radical cascades.

Keywords:
non‐Kekulé hydrocarbonperi‐fusionsteric effectstrianguleneπ‐radical cascade

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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

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Last Updated: May 15, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Open-shell molecular graphene fragments are promising building blocks for carbon nanostructures due to their radical cascade potential.
  • Limited understanding of graphene π-radical reactivity hinders their synthetic application, particularly controlling reactions with multiple reactive centers.

Purpose of the Study:

  • To establish reaction control in systems with multiple unpaired π-electrons, specifically focusing on open-shell molecular graphene fragments.
  • To investigate the role of reactive intermediates in dictating selectivity during oxidative peri-fusion reactions.
  • To demonstrate the synthetic utility of controlled graphene π-radical reactivity.

Main Methods:

  • Examined the oxidative peri-fusion of the dihydro-precursor of triangulene, a non-Kekulé hydrocarbon.
  • Investigated reactive intermediates to understand selectivity.
  • Utilized precise placement of steric bulk to modulate reactivity and control product formation.

Main Results:

  • Demonstrated that monoradical intermediates, not diradical, are key to reaction selectivity.
  • Showed that steric bulk effectively steers selectivity towards doubly or singly peri-fused dimeric products.
  • Established a method for controlling reactions involving open-shell molecular graphene fragments.

Conclusions:

  • Controlled reactivity of open-shell molecular graphene fragments is achievable and synthetically valuable.
  • This approach offers a step-economic route to complex graphene-based carbon nanostructures.
  • Understanding and controlling π-radical intermediates is crucial for advancing graphene synthesis.