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Jaulas orgánicas quirales con una estructura helicoidal de tres hilos derivada del heliceno

Abaid Ullah Malik¹, Fuwei Gan², Chengshuo Shen²

¹School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , Shanghai 200240, China.

Journal of the American Chemical Society

|February 10, 2018

Resumen

Los investigadores crearon nuevas jaulas orgánicas covalentes utilizando heliceno

Área de la Ciencia:

Química supramolecular
Química orgánica
Ciencias de los materiales

Sus antecedentes:

Los helicenos poseen una quiralidad inherente debido a su estructura helicoidal única.
Las jaulas orgánicas covalentes (COC) son materiales porosos con propiedades sintonizables.
El desarrollo de COCs quirales es crucial para las aplicaciones enantioselectivas.

Objetivo del estudio:

Para sintetizar nuevas jaulas orgánicas covalentes utilizando bloques de construcción de heliceno.
Investigar las propiedades estructurales y quirales de los COC resultantes.
Evaluar las capacidades de adsorción enantioselectiva de los COCs quirales.

Principales métodos:

Se emplearon reacciones de condensación de imina para construir los COC.
Se utilizó la espectroscopia de resonancia magnética nuclear de protones (RMN) para confirmar la integridad estructural y la diastereotopía.
Se utilizó la espectroscopia de dicroísmo circular (CD) para analizar las propiedades quirales.
Se realizaron experimentos de adsorción quiral con racematos aromáticos.

Principales resultados:

Se sintetizó con éxito una jaula orgánica covalente de tipo [3+2] con una estructura helicoidal de triple cadena.
La quiralidad intrínseca de las unidades de heliceno se conservó en los COC, exhibiendo un marco retorcido similar a una hélice.
La quiralidad estructural se mantuvo en la solución, evidenciada por una diastereotopía significativa en RMN y efectos de algodón distintos en los espectros de CD.
Los COCs quirales demostraron una notable enantioselectividad en la adsorción de varios racematos aromáticos.

Conclusiones:

Las jaulas orgánicas covalentes a base de heliceno se pueden preparar eficazmente mediante la condensación de imina.
Los COC sintetizados exhiben una robusta quiralidad estructural, retenida en la solución.
Estas jaulas orgánicas quirales son prometedoras para aplicaciones de separación y reconocimiento enantioselectivos.

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