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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: Electrophilic Radicals01:02

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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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.2K
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

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...
2.0K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
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 Formation: Addition00:47

Radical Formation: Addition

1.8K
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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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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S-Containing Double Helicenes Featuring Robust Radical Cations.

Li Zhang1,2, Man Gao1, Shilong Su1

  • 1Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 28, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed stable, sulfur-containing double helicenes that form robust radical cations. These molecules show potential for organic electronics due to their unique π-conjugated structures and conductivity.

Keywords:
S‐heterocycledouble heliceneorganic conductorradical cation

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Double helicenes are π-conjugated systems with potential applications in organic electronics.
  • Developing stable radical cations from such systems is challenging.
  • Sulfur incorporation can influence electronic properties and molecular packing.

Purpose of the Study:

  • To synthesize novel sulfur-containing double helicenes.
  • To investigate the formation and stability of their radical cations.
  • To evaluate their potential for organic electronic applications.

Main Methods:

  • Scholl reaction for synthesis of sulfur-containing [7]helicene.
  • X-ray crystallography and Density Functional Theory (DFT) calculations for structural analysis.
  • Chemical oxidation with nitrosonium, Electron Paramagnetic Resonance (EPR) spectroscopy, and absorption spectroscopy for characterization of radical cations.
  • Conductivity measurements of radical cation salts.

Main Results:

  • Successful synthesis of two S-containing double helicenes.
  • Confirmation of twisted conformations via X-ray crystallography and DFT.
  • Generation of stable π-conjugated radical cations, verified by EPR spectroscopy.
  • Observation of π-stacked columns in crystal structures.
  • Room-temperature conductivity up to 0.16 S cm⁻¹ for a radical cation salt.

Conclusions:

  • S-containing double helicenes are a viable platform for creating stable π-conjugated radical cations.
  • The π-π interactions in these systems are preserved, crucial for conductivity.
  • These findings open avenues for designing advanced materials for organic electronics.