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Análogos de trifenileno con núcleos B2N2C2: síntesis, estructura, comportamiento redox y propiedades fotofísicas
Cory A Jaska1, David J H Emslie, Michael J D Bosdet
1Department of Chemistry, University of Calgary, 2500 University Drive North West, Calgary, Alberta, Canada T2N 1N4.
Journal of the American Chemical Society
|August 17, 2006
Resumen
Se sintetizaron nuevos análogos heteroaromáticos de trifenileno con núcleos B(2) N(2) C(2). Estos compuestos exhiben una variedad de aromaticidad y propiedades estructurales, que influyen en su comportamiento electrónico y fluorescencia.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Ciencia de los materiales Ciencia de los materiales.
- Química supramolecular de las moléculas.
Sus antecedentes:
- Los análogos del trifenileno son de interés por sus propiedades electrónicas y estructurales únicas.
- Los compuestos heteroaromáticos que contienen boro y nitrógeno ofrecen características sintonizables para materiales avanzados.
Objetivo del estudio:
- Para sintetizar nuevos análogos heteroaromáticos de trifenileno B(2) N(2) C(2).
- Investigar las propiedades estructurales, electrónicas y fotofísicas de estos nuevos compuestos.
Principales métodos:
- Quelación de los derivados de piridazina con los precursores del diborabifenilo.
- Cálculos del Cambio Químico Nuclear Independiente (NICS) para la evaluación de la aromaticidad.
- Cristalografía de rayos X para el análisis estructural.
- Espectroscopia de resonancia paramagnética de electrones (EPR) para la caracterización de aniones radicales.
Principales resultados:
- Análogos de trifenileno sintetizados con alquilo, arilo y B(2)N(2)C(2) anulados por benzo.
- Los cálculos del NICS indicaron una alta aromaticidad en los anillos de borabenzeno y una no aromaticidad en los anillos de piridazina.
- Las estructuras planas se formaron con caras de piridazina no sustituidas, mientras que la sustitución indujo núcleos retorcidos.
- Embalaje de hueso de arenque dimérico observado en especies planas debido a las interacciones B...N intermoleculares.
- Se generaron y caracterizaron aniones radicales.
- Los análogos planos mostraron una fluorescencia débil, mientras que los análogos retorcidos no eran fluorescentes.
Conclusiones:
- El núcleo B(2)N(2)C(2) permite la síntesis de diversos análogos del trifenileno.
- Las variaciones estructurales tienen un impacto significativo en las propiedades electrónicas y la fluorescencia.
- Las interacciones intermoleculares juegan un papel en el empaque y las propiedades del estado sólido.
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