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Síntesis de nanografenos estables con bordes en zigzag dopados con OBO basados en la desmetilación en tándem y la
Xiao-Ye Wang1, Akimitsu Narita1, Wen Zhang1
1Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
Journal of the American Chemical Society
|July 5, 2016
Resumen
Los investigadores desarrollaron una nueva síntesis para los bistetracenos y peritetracenos dopados con OBO. Estos nuevos nanografenes dopados con heteroátomos muestran una mayor estabilidad y fluorescencia, ofreciendo nuevas posibilidades en la ciencia de los materiales.
Área de la Ciencia:
- Química orgánica
- Ciencias de los materiales
- Nanotecnología
Sus antecedentes:
- Los hidrocarburos aromáticos policíclicos de todo carbono como los bistetracenos a menudo sufren de inestabilidad.
- El desarrollo de estructuras de nanografeno estables y funcionales es crucial para las aplicaciones de materiales avanzados.
Objetivo del estudio:
- Desarrollar una nueva estrategia sintética para los tetrabenzo[a,f,j,o]perilenos (bistetracenos) y los tetrabenzo[bc,ef,kl,no]coronenos (peritetracenos) dopados con OBO.
- Investigar las propiedades estructurales, electrónicas y fotofísicas de estos nuevos nanografenos dopados con heteroátomos.
Principales métodos:
- Para la síntesis se empleó una estrategia de desmetilación- arilación en tándem.
- Se utilizó un análisis de rayos X monocristalino para determinar la estructura molecular.
- Se realizaron reacciones de ciclodehidrogenación para acceder a los derivados del peritetraceno.
Principales resultados:
- Se han sintetizado con éxito análogos de bistetraceno y peritetraceno dopados con OBO.
- Los bistetracenos dopados con OBO demostraron una excelente estabilidad y una fuerte fluorescencia, a diferencia de sus contrapartes de carbono.
- El análisis de rayos X reveló una estructura de doble [5] heliceno retorcida para el bistetraceno dopado con OBO, lo que confirma su aplicabilidad a los nuevos heterohelicenos.
- Se logró la síntesis de peritetracenos dopados con heteroátomos sin precedentes con bordes en zigzag estables.
Conclusiones:
- La estrategia desarrollada en tándem de desmetilación y borilación de arilo es eficaz para la síntesis de nuevos nanografenos dopados con OBO.
- El dopaje heteroatómico mejora significativamente la estabilidad y la fluorescencia de las estructuras de bistetraceno y peritetraceno.
- Este trabajo abre nuevas vías para diseñar y sintetizar nanografenes estables y funcionales de tipo periceno.
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