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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Introduction
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Las impurezas en los ésteres arilborónicos inducen un resplandor persistente

Zhu Wu1,2, Christoph Herok3, Alexandra Friedrich1

  • 1Institute of Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

Journal of the American Chemical Society
|November 5, 2024
PubMed
Resumen

La fosforescencia a temperatura ambiente (RTP) en los ésteres arilborónicos a menudo se debe a las impurezas, no a los compuestos en sí mismos. La purificación cuidadosa eliminó el RTP, pero se encontró que una impureza específica inducía un resplandor prolongado.

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Área de la Ciencia:

  • Química orgánica
  • La fotofísica
  • Ciencias de los materiales

Sus antecedentes:

  • Informes recientes sugieren que los ésteres arilborónicos exhiben fosforescencia a temperatura ambiente (RTP), lo que desafía las teorías establecidas de cruce entre sistemas.
  • Esta propiedad es valiosa para aplicaciones como impresión de seguridad, detección de oxígeno e imágenes biológicas.

Objetivo del estudio:

  • Investigar la validez de la RTP en los ésteres arilborónicos.
  • Determinar si los fenómenos RTP observados son propiedades intrínsecas o artefactos de las impurezas.

Principales métodos:

  • Síntesis y purificación de 12 ésteres arilborónicos activos en RTP previamente reportados mediante cromatografía, recristalización y sublimación.
  • Reexamen de las propiedades fotofísicas, difracción de rayos X de un solo cristal y estudios teóricos.
  • Aislamiento e identificación de la impureza responsable del retraso en la fluorescencia.

Principales resultados:

  • Ninguno de los 12 ésteres arilborónicos purificados exhibió RTP persistente.
  • La impureza 4-amino-3,5-bis ((pinacolatoboril) benzonitrilo fue identificada como la fuente de fluorescencia retrasada en el 3,5-bis ((pinacolatoboril) benzonitrilo.
  • El dopaje con 1.0 mol% de la impureza indujo un resplandor de 67 ms a través de un estado de transferencia de carga de dímeros.

Conclusiones:

  • La RTP observada en estudios previos de ésteres arilborónicos probablemente fue el resultado de impurezas.
  • La purificación rigurosa es crucial para una investigación fotofísica precisa.
  • Se ha demostrado una estrategia para diseñar materiales con resplandor prolongado mediante dopaje controlado con impurezas específicas.