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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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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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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Mejora simultánea del potencial redox y la estabilidad de los católitos orgánicos multiredox mediante la

Yichao Yan1,2, Sophia G Robinson3,2, Thomas P Vaid1,2

  • 1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Journal of the American Chemical Society
|August 13, 2021
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Resumen

Se desarrollaron nuevos católitos orgánicos utilizando sustituyentes de diaminociclopropenio (DAC) para baterías de flujo redox no acuosas. Estas moléculas modificadas por DAC permiten voltajes más altos y ciclos estables, avanzando en soluciones de almacenamiento de energía.

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Área de la Ciencia:

  • La electroquímica
  • Ciencias de los materiales
  • Almacenamiento de energía

Sus antecedentes:

  • Las baterías de flujo redox no acuosas requieren católitos orgánicos estables con altos potenciales redox.
  • Los núcleos de fenazina y fenotiazina ofrecen un potencial redox moderado pero una reversibilidad limitada.

Objetivo del estudio:

  • Desarrollar nuevos católitos orgánicos con mayor potencial redox y estabilidad.
  • Investigar el efecto de los sustituyentes de diaminociclopropenio (DAC) en las propiedades redox de la fenotiazina y la fenotiazina.

Principales métodos:

  • Síntesis de fenozina y derivados de fenotiazina funcionalizados con sustituyentes de DAC.
  • Caracterización electroquímica mediante la voltametría cíclica.
  • Pruebas en configuraciones de baterías de flujo redox no acuoso de dos electrones.

Principales resultados:

  • Los sustituyentes DAC aumentaron los potenciales redox en ~ 300 mV y mejoraron la reversibilidad.
  • El derivado de la fenotiazina exhibió una oxidación reversible a 1,20 V frente a Fc/Fc+.
  • Las baterías de flujo redox alcanzaron tensiones de hasta 2,0 V sin cruce detectable durante 250 ciclos.

Conclusiones:

  • Las fenozinas y fenotiazinas funcionalizadas con diaminociclopropenio son catolitos orgánicos estables y de alto potencial.
  • Los efectos de retirada de electrones y estabilización de resonancia del grupo DAC son clave para el rendimiento.
  • Estos materiales demuestran el potencial para baterías de flujo redox no acuosas eficientes y duraderas.