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Dos isósteros BN del antraceno: síntesis y caracterización

Jacob S A Ishibashi¹, Jonathan L Marshall, Audrey Mazière

¹Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.

Journal of the American Chemical Society

|October 3, 2014

Resumen

Los investigadores sintetizaron los antracenos BN y descubrieron que la incorporación de boro y nitrógeno estabiliza los niveles de energía de los orbitales moleculares ocupados más altos (HOMO). Esta estrategia de diseño molecular mantiene la brecha de banda óptica, ofreciendo nuevas posibilidades para la estabilización del material.

Área de la Ciencia:

Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.
La espectroscopia es una técnica de espectroscopia.

Sus antecedentes:

Las estructuras de tipo aceno son fundamentales en la electrónica orgánica.
El ajuste de las propiedades electrónicas de los acenos es crucial para aplicaciones avanzadas.
El isosterismo de boro-nitrógeno (BN) ofrece una vía para modificar los marcos moleculares.

Objetivo del estudio:

Para sintetizar y caracterizar los antracenos BN.
Para comparar su estructura electrónica y reactividad con el antraceno de todo carbono.
Explorar el isosterismo BN/CC como una estrategia de diseño molecular.

Principales métodos:

Síntesis de los antracenos 1 y 2 de BN.
Espectroscopia de fotoelectrones UV en fase gaseosa para la determinación de la energía HOMO.
Espectroscopia de absorción y emisión UV-vis para propiedades ópticas.
Estudios de reactividad que incluyen la cicloadición, la acilación de Friedel-Crafts y la brominación electrófila.

Principales resultados:

Tendencia de energía HOMO: antraceno (-7,4 eV) < antraceno BN 1 (-7,7 eV) < antraceno bis-BN 2 (-8,0 eV).
La brecha de banda óptica se mantuvo sin cambios en toda la serie, con emisión a 403 nm.
Los antracenos de BN mostraron una mayor estabilidad frente a las reacciones de cicloadición y Friedel-Crafts.
La brominación regioselectiva se produjo en la posición 9 del antraceno 1 de BN.

Conclusiones:

La incorporación de BN estabiliza el nivel de energía HOMO de los derivados del antraceno.
La brecha de banda óptica se mantiene a pesar de la sustitución de BN.
El isosterismo BN/CC es una estrategia eficaz para estabilizar las estructuras de tipo aceno.
La estructura electrónica dicta la reactividad y la regioselectividad de los antracenos BN.

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