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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...
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Radical Formation: Homolysis00:54

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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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:
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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: Addition00:47

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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 Reactivity: Electrophilic Radicals01:02

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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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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Mechanical-Bond-Protected, Air-Stable Radicals.

Junling Sun, Zhichang Liu, Wei-Guang Liu1

  • 1Materials and Process Simulation Center, California Institute of Technology , Pasadena, California 91125, United States.

Journal of the American Chemical Society
|August 15, 2017
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Summary
This summary is machine-generated.

Researchers created novel [2]catenanes, which are mechanically interlocked molecules, using radical templation. These molecules exhibit multiple stable redox states, showing promise for high-density data memory applications.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Radical templation is a method for constructing complex molecular architectures.
  • Catenanes are mechanically interlocked molecules with unique topological properties.
  • Developing materials with multiple redox states is crucial for advanced electronic applications.

Purpose of the Study:

  • To synthesize novel [2]catenanes using a heterotrisradical tricationic inclusion complex.
  • To characterize the electronic and structural properties of the synthesized catenanes.
  • To evaluate the potential of these catenanes for high-density data memory.

Main Methods:

  • Radical templation using a disubstituted 4,4'-bipyridinium radical cation (DB•+) and an asymmetric cyclophane bisradical dication (DAPQT2(•+)).
  • Isolation and characterization of symmetric and asymmetric [2]catenanes (SC·7PF6 and AC·7PF6) by EPR spectroscopy and X-ray crystallography.
  • Electrochemical studies (cyclic voltammetry) to determine the number of accessible redox states.

Main Results:

  • Successful synthesis of symmetric (SC·7PF6) and asymmetric (AC·7PF6) [2]catenanes.
  • Characterization revealed air-stable monoradicals with delocalized unpaired electrons across inner 4,4'-bipyridinium (BIPY2+) units, forming a mixed-valence (BIPY2)•3+ state.
  • Electrochemical studies demonstrated access to five, six, and seven redox states in related catenanes by incorporating diazapyrenium dication (DAP2+) units.

Conclusions:

  • The synthesized [2]catenanes are stable radical species with tunable electronic properties.
  • The ability to access multiple redox states makes these catenanes promising candidates for high-density data storage.
  • This work presents a novel approach for designing molecular materials for advanced memory technologies.