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Acoplamiento de dinitrilo mediado por titanoceno: una ruta divergente hacia hidrocarburos aromáticos policíclicos que

Gavin R Kiel¹, Adrian E Samkian¹, Amélie Nicolay¹

¹Department of Chemistry, University of California, Berkeley , Berkeley, California 94720, United States.

Journal of the American Chemical Society

|February 1, 2018

Resumen

Los investigadores han desarrollado un nuevo método para sintetizar grandes hidrocarburos aromáticos policíclicos (HAP) que contienen nitrógeno. Esta estrategia permite un control preciso de las propiedades finales de estas moléculas orgánicas complejas.

Área de la Ciencia:

Síntesis orgánica
Ciencias de los materiales
Química supramolecular

Sus antecedentes:

Los hidrocarburos aromáticos policíclicos (HAP) que contienen nitrógeno son cruciales en la ciencia de los materiales.
El desarrollo de estrategias sintéticas generales para los HAP grandes y funcionalizados sigue siendo un desafío.

Objetivo del estudio:

Informar sobre una nueva estrategia sintética general para la construcción de grandes HAP que contengan nitrógeno.
Demostrar la funcionalidad de última etapa para ajustar las propiedades fotofísicas y electroquímicas.

Principales métodos:

Ciclización reductiva mediada por el titanoceno de los precursores de oligo ((dinitrilo)).
Reacciones divergentes de transferencia de titanoceno para la instalación de unidades funcionales.
Análisis espectroscópicos (UV/vis, fluorescencia), electroquímicos (voltametría cíclica) y computacionales (DFT).

Principales resultados:

Síntesis exitosa de diversos HAP que contienen nitrógeno mediante una estrategia en dos etapas.
Instalación demostrada en fase avanzada de unidades de o-quinona, diazol y pirazina.
Establecimiento de un control racional sobre los niveles de energía HOMO/LUMO y las propiedades asociadas.

Conclusiones:

La metodología presentada proporciona una plataforma versátil para el diseño de nuevos materiales basados en HAP.
Destaca la utilidad de los intermediarios de di ((aza) metallaciclopentadieno en la síntesis orgánica.
Permite la primera formación formal de anillos de pirazina [2 + 2 + 2] a través de esta ruta.

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