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5,14-Diaryldiindeno[2,1-f:1',2' -j]piceno: un nuevo heliceno estable [7] con un carácter parcialmente biradical
Ya-Chu Hsieh1, Cheng-Feng Wu1, Yi-Ting Chen
1Department of Chemistry , National Cheng Kung University , 70101 Tainan , Taiwan.
Journal of the American Chemical Society
|October 23, 2018
Resumen
Los investigadores sintetizaron un areno helicoidal estable, el 5,14-Diaryldiindeno[2,1-f:1
Área de la Ciencia:
- Química orgánica
- Ciencias de los materiales
- Química supramolecular
Sus antecedentes:
- Las arenas helicoidales son moléculas orgánicas complejas con propiedades estructurales y electrónicas únicas.
- El desarrollo de compuestos helicoidales térmicamente y químicamente estables es crucial para aplicaciones avanzadas.
Objetivo del estudio:
- Para sintetizar y caracterizar un nuevo areno helicoidal, el 5,14-Diaryldiindeno[2,1-f:1',2' -j]piceno (DDP).
- Investigar las propiedades estructurales, térmicas y electrónicas del DDP y sus derivados.
Principales métodos:
- Síntesis orgánica en varios pasos a partir del 1,4-bis[2-arylethynyl) fenil]benceno.
- Cristalografía de rayos X para la verificación estructural de la columna vertebral helicoidal.
- Técnicas espectroscópicas (ESR, UV-Vis-NIR) y fabricación de dispositivos para la evaluación de las propiedades.
Principales resultados:
- Síntesis exitosa de DDP en cuatro pasos.
- La cristalografía de rayos X confirmó la estructura helicoidal con una alta barrera a la racemización (> 50 kcal / mol).
- Los derivados de DDP exhiben una pequeña brecha HOMO-LUMO (1,31 eV), actividad ESR y una amplia fotoabsorción de UV a NIR.
- Transporte de carga ambipolar demostrado en transistores orgánicos de efecto de campo procesados en solución.
Conclusiones:
- El 5,14-Diaryldiindeno[2,1-f:1',2' -j]piceno es un areno helicoidal térmico y químicamente estable con propiedades optoelectrónicas prometedoras.
- La estructura helicoidal única contribuye a las altas barreras de racimización y las funcionalidades versátiles.
- El DDP representa una nueva clase de materiales valiosos para la electrónica orgánica y la fotónica.
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