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Triticenos aromáticos policíclicos: estrategias de ciclización de sustitución de oxígeno por sustitución de oxígeno.

Brett VanVeller¹, Derek J Schipper, Timothy M Swager

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Journal of the American Chemical Society

|April 19, 2012

Resumen

Los investigadores lograron la ciclización y la planarización de hidrocarburos aromáticos policíclicos utilizando catálisis ácida y reacciones radicales. El andamio de triptíceno permitió nuevos sistemas π rígidos para el desarrollo de materiales avanzados.

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Área de la Ciencia:

Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

Los hidrocarburos aromáticos policíclicos (HAP) son bloques de construcción cruciales para los materiales avanzados.
El desarrollo de métodos sintéticos para la funcionalización controlada de HAP sigue siendo un desafío.

Objetivo del estudio:

Para sintetizar nuevos y rígidos sistemas π a partir de HAP.
Para ampliar la utilidad de las moléculas basadas en triptíceno para la ciencia de los materiales.

Principales métodos:

Reacciones de transeterificación catalizadas por ácido.
Reacciones de radicales de oxígeno para la ciclización y la planarización.
Utilizando el andamio de triptíceno para dirigir la reactividad.

Principales resultados:

Ciclización y planarización exitosas de los HAP.
Incorporación de sustitutos de oxígeno en la estructura de los HAP.
Formación de sistemas π rígidos facilitados por el andamio triptceno.

Conclusiones:

El método desarrollado proporciona una nueva ruta a los HAP funcionalizados y rígidos.
Las moléculas basadas en triptíceno ofrecen mayores posibilidades para aplicaciones de materiales.
Este trabajo mejora el conjunto de herramientas sintéticas para el diseño de nuevos sistemas π-conjugados.