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Fotoswitches de arylazoindazol: Fácil síntesis y funcionalidad a través de S_NAr sustitución

Raquel Travieso-Puente¹, Simon Budzak², Juan Chen¹

¹Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 AG Groningen, The Netherlands.

Journal of the American Chemical Society

|February 21, 2017

Resumen

Los investigadores desarrollaron una nueva vía sintética para crear arylazoindazoles. Estos nuevos fotointerruptores azoicos exhiben una excelente resistencia a la fatiga y estabilidad, con potencial para una mayor modificación química.

Área de la Ciencia:

Química orgánica
Ciencias de los materiales
La fotoquímica

Sus antecedentes:

Los arylazoindazoles son una clase de compuestos con aplicaciones potenciales en la tecnología de interruptores fotográficos.
El desarrollo de rutas sintéticas eficientes y la comprensión de sus propiedades fotoquímicas son cruciales para avanzar en este campo.

Objetivo del estudio:

Para presentar una ruta sintética directa a una nueva clase de arylazoindazoles.
Investigar la isomerización fotoquímica, la resistencia a la fatiga y la estabilidad térmica de estos nuevos compuestos.
Explorar el potencial para una mayor funcionalización de la fracción de indazol fluorado.

Principales métodos:

Síntesis de arylazoindazoles mediante sustitución aromática nucleofílica (S_NAr).
Deprotonación de una forma sustituida por C6 y F5 para inducir la ciclización.
Estudios de isomerización fotoquímica para evaluar la fotorrespuesta y la resistencia a la fatiga.
Mediciones de la estabilidad térmica de los isómeros Z.

Principales resultados:

Se estableció una vía sintética fácil para los arylazoindazoles utilizando S_NAr intermolecular.
Los fotointerruptores de azo sintetizados demostraron una alta resistencia a la fatiga y una isomerización fotoquímica eficiente.
Los isómeros Z exhibieron largas vidas medias térmicas (hasta varios días) a temperatura ambiente.
El grupo de indazol fluorado permitió reacciones de desplazamiento nucleófilo subsecuentes.

Conclusiones:

Se ha desarrollado una estrategia sintética novedosa y eficiente para los arylazoindazoles.
Estos compuestos representan una nueva clase prometedora de fotointerruptores azoicos con excelente estabilidad y propiedades sintonizables.
La accesibilidad sintética y el potencial de funcionalidad abren vías para diversas aplicaciones en la ciencia de los materiales y más allá.

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