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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

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: Addition00:47

Radical Formation: Addition

2.4K
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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π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

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Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

5.3K
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...
5.3K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.6K
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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An M2 L4 Molecular Capsule with a Redox Switchable Polyradical Shell.

Kohei Yazaki1, Shogo Noda1, Yuya Tanaka1

  • 1Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama, 226-8503, Japan.

Angewandte Chemie (International Ed. in English)
|October 30, 2016
PubMed
Summary

Researchers synthesized a novel molecular capsule with a polyradical framework, overcoming challenges in creating such nanostructures. This stable tetra(radical cation) capsule demonstrates new possibilities in advanced materials science.

Keywords:
capsulescoordination chemistrydihydrophenazineradical cationsredox systems

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Synthesizing molecular nanostructures with polyradical frameworks is synthetically challenging.
  • Existing methods for neutral and ionic nanostructures are not directly applicable to polyradical systems.

Purpose of the Study:

  • To report the quantitative formation of a new M2L4 molecular capsule with a polyradical framework.
  • To explore the electrochemical properties and stability of the synthesized nanostructure.

Main Methods:

  • Self-assembly of metal ions and dihydrophenazine-based ligands.
  • Electrochemical oxidation to generate radical cations.
  • Chemical oxidation for comparison.

Main Results:

  • A M2L4 molecular capsule with a spherical nanocavity (approx. 1 nm diameter) was successfully synthesized.
  • The capsule shell consists of eight redox-active dihydrophenazine panels.
  • Electrochemical oxidation generated multiple radical cations on the capsule shell.
  • A stable tetra(radical cation) capsule was reversibly formed via chemical and electrochemical oxidation.

Conclusions:

  • The study presents a viable synthetic route to polyradical molecular nanostructures.
  • The novel capsule exhibits tunable redox properties and potential applications in advanced materials.
  • Reversible formation of the tetra(radical cation) state highlights the stability and control achievable.