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Related Concept Videos

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: Steric Effects01:10

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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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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.0K
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 Formation: Addition00:47

Radical Formation: Addition

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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.
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Radical Formation: Overview01:03

Radical Formation: Overview

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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 Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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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...
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Stable π-Extended Thio[7]helicene-Based Diradical with Predominant Through-Space Spin-Spin Coupling.

Hao Wu1, Hiroki Hanayama2, Max Coehlo3

  • 1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.

Journal of the American Chemical Society
|March 6, 2024
PubMed
Summary

Researchers synthesized a stable, chiral diradicaloid molecule, ET7H-R, featuring unique π-conjugation. This molecule exhibits significant through-space spin-spin coupling, paving the way for new molecular electronics research.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Molecular Physics

Background:

  • Helicenes are chiral aromatic compounds with unique electronic properties.
  • Stable open-shell diradicals are of interest for molecular magnetism and spintronics.
  • Investigating through-space spin-spin coupling (TSC) is crucial for understanding intramolecular magnetic interactions.

Purpose of the Study:

  • To synthesize a novel π-extended thiohelicene scaffold capable of hosting stable radicals.
  • To characterize the electronic and magnetic properties of the resulting open-shell helical diradical, ET7H-R.
  • To explore the phenomenon of through-space spin-spin coupling in a chiral helical system.

Main Methods:

  • Multi-step organic synthesis to construct the π-extended thio[7]helicene scaffold.
  • Functionalization with bulky phenoxy radicals to create the diradical.
  • Variable-temperature continuous-wave electron spin resonance (cw-ESR) spectroscopy.
  • Superconducting quantum interference device (SQUID) magnetometry.

Main Results:

  • Successful synthesis of a stable, air-stable open-shell helical diradical (ET7H-R) with high diradical character (y0 = 0.998).
  • Demonstration of nontrivial π conjugation and persistent chirality in the helical structure.
  • Observation of predominant through-space spin-spin coupling between radicals at helical terminals.
  • Identification of a singlet ground state with a nearly degenerate triplet state via variable-temperature ESR and SQUID magnetometry.

Conclusions:

  • Stable helical diradicaloids are viable platforms for fundamental studies of intramolecular through-space spin-spin coupling.
  • The synthesized ET7H-R molecule provides a unique system for investigating spin interactions in chiral environments.
  • This work opens avenues for designing novel organic materials with tailored magnetic and electronic properties.