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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.
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Radicals: Electronic Structure and Geometry01:07

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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.
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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

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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 Formation: Overview01:03

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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:
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Radical Formation: Abstraction00:47

Radical Formation: Abstraction

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The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Highly Conducting and Flexible Radical Crystals.

Taeyeon Kwon1, Jin Young Koo1, Hee Cheul Choi1

  • 1Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673, Republic of Korea.

Angewandte Chemie (International Ed. in English)
|June 16, 2020
PubMed
Summary

Researchers developed a flexible and conductive organic radical crystal using 9,10-bis(phenylethynyl)anthracene radical cation (BPEA). This breakthrough addresses the challenge of combining flexibility and conductivity in organic electronics.

Keywords:
conducting radical crystalscrystal growthelectrocrystallizationflexible radical crystalsradicals

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Crystallography

Background:

  • High conductivity and flexibility are crucial for advanced organic electronic components.
  • Achieving both properties simultaneously in crystalline organic materials is challenging due to inherent brittleness.

Purpose of the Study:

  • To report a novel organic radical crystal system exhibiting both high flexibility and high electrical conductivity.
  • To investigate the structural basis for the observed properties.

Main Methods:

  • Synthesis and characterization of an organic radical crystal based on 9,10-bis(phenylethynyl)anthracene radical cation (BPEA).
  • Measurement of electrical conductivity under both linear and bent conditions.
  • Structural analysis to determine key intermolecular interactions.

Main Results:

  • The BPEA radical crystal demonstrated high electrical conductivity (2.68 S/cm linear, 2.43 S/cm bent) under ambient conditions.
  • The crystal exhibited significant flexibility under applied pressure.
  • Structural analysis revealed a short π-π stacking distance (3.290 Å) between BPEA units and the role of PF6- counter ions.

Conclusions:

  • The developed organic radical crystal successfully combines high flexibility and high conductivity.
  • Short π-π stacking and specific counter ions are key factors enabling these properties in the BPEA system.
  • This material holds promise for next-generation flexible organic electronic applications.