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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

Radical Formation: Homolysis

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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:
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: 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 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.
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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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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Radicales estables en el aire protegidos por enlaces mecánicos

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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Resumen

Los investigadores crearon nuevas [2]catenanas, que son moléculas mecánicamente entrelazadas, utilizando la templación radical. Estas moléculas exhiben múltiples estados redox estables, mostrando una promesa para aplicaciones de memoria de datos de alta densidad.

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Área de la Ciencia:

  • Química supramolecular
  • Ciencias de los materiales
  • La electroquímica

Sus antecedentes:

  • La templación radical es un método para construir arquitecturas moleculares complejas.
  • Las catenanas son moléculas mecánicamente entrelazadas con propiedades topológicas únicas.
  • El desarrollo de materiales con múltiples estados redox es crucial para aplicaciones electrónicas avanzadas.

Objetivo del estudio:

  • Para sintetizar nuevos [2]catenanos utilizando un complejo de inclusión tricationico heterotrádico.
  • Caracterizar las propiedades electrónicas y estructurales de los catenanos sintetizados.
  • Evaluar el potencial de estos catenanos para la memoria de datos de alta densidad.

Principales métodos:

  • Templación de radicales mediante el uso de un catión radical de 4,4'-bipiridinio disuelto (DB•+) y un catión bisradical ciclófano asimétrico (DAPQT2(•+)).
  • Aislamiento y caracterización de las cadenas simétricas y asimétricas [2] (SC·7PF6 y AC·7PF6) por espectroscopia EPR y cristalografía de rayos X.
  • Estudios electroquímicos (voltametría cíclica) para determinar el número de estados redox accesibles.

Principales resultados:

  • Síntesis exitosa de las cadenas simétricas (SC·7PF6) y asimétricas (AC·7PF6) [2].
  • La caracterización reveló monorrádicos estables en el aire con electrones no apareados deslocalizados a través de unidades internas de 4,4'-bipiridinium (BIPY2+), formando un estado de valencia mixta (BIPY2) • 3+.
  • Los estudios electroquímicos demostraron el acceso a cinco, seis y siete estados redox en catenanos relacionados mediante la incorporación de unidades de dication de diazapirenio (DAP2+).

Conclusiones:

  • Los catenanos sintetizados [2] son especies radicales estables con propiedades electrónicas sintonizables.
  • La capacidad de acceder a múltiples estados redox hace que estos catenanos sean candidatos prometedores para el almacenamiento de datos de alta densidad.
  • Este trabajo presenta un nuevo enfoque para el diseño de materiales moleculares para tecnologías avanzadas de memoria.