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Derivados de arilalquinilaftaleno que emiten azul a través de una reacción en cascada de hexadehidro-diels-alder

Feng Xu¹, Kyle W Hershey¹, Russell J Holmes¹

¹Department of Chemistry and ‡Department of Chemical Engineering and Materials Science, University of Minnesota , Minneapolis, Minnesota 55455, United States.

Journal of the American Chemical Society

|September 15, 2016

Resumen

Tres nuevos naftalenos sustituidos por alquinilo exhiben una luminiscencia azul profundo, adecuada para diodos emisores de luz orgánicos (OLED). Su síntesis es eficiente, y las propiedades son estables en diferentes sustituyentes, lo que sugiere potencial para materiales electrónicos avanzados.

Área de la Ciencia:

Química orgánica
Ciencias de los materiales
La fotofísica

Sus antecedentes:

Los derivados del naftaleno son cruciales en el desarrollo de materiales avanzados.
Los diodos orgánicos emisores de luz (OLED) requieren componentes emisores eficientes.
Los emisores de color azul profundo son particularmente buscados para las tecnologías de visualización.

Objetivo del estudio:

Síntesis y caracterización de nuevos naftalenos sustituidos por alquinilo.
Evaluar sus propiedades de luminiscencia para posibles aplicaciones de OLED.
Investigar la influencia de los sustituyentes en las características fotofísicas.

Principales métodos:

Síntesis a través de una secuencia de tres pasos que incluye la cicloisomerización hexadehidro-Diels-Alder (HDDA).
Captura de un intermediario de benzina con tetrafenilciclopentadienona.
Mediciones de la fotoluminiscencia y la electroluminiscencia en soluciones y películas sólidas.

Principales resultados:

Se han sintetizado con éxito tres naftalenos sustituidos por alquinilo.
Los compuestos exhiben una fuerte luminiscencia azul profundo bajo estimulación óptica y eléctrica.
Las propiedades fotofísicas mostraron una sensibilidad mínima a las variaciones de los sustituyentes electrónicos (H, OMe, CO2Me).
Es probable que los grupos arilo retorcidos reduzcan las interacciones intermoleculares, mejorando la estabilidad del material.

Conclusiones:

Los naftalenos sustituidos por alquinilo son candidatos prometedores para los emisores de color azul profundo en los OLED.
La vía sintética es eficiente y versátil.
Las características estructurales contribuyen a propiedades fotofísicas favorables y a la estabilidad del material.

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