Redes concertadas de enlaces halógenos con bromuros de N-alquilo amonio resorcinareno: desde el dumbbell dimérico hasta las arquitecturas cápsulas

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Fangfang Pan¹, Ngong Kodiah Beyeh¹, Kari Rissanen¹

¹Department of Chemistry, Nanoscience Center, University of Jyvaskyla, P.O. Box. 35, FI-40014 Jyvaskyla yliopisto, Finland.

Journal of the American Chemical Society

|July 28, 2015

Resumen

Los cambios sutiles en los sustituyentes de N-alquilo amonio resorcinareno bromuro crean diversas arquitecturas supramoleculares. Estas estructuras, impulsadas por enlaces halógenos, van desde cápsulas hasta complejas redes 3D, que muestran un autoensamblaje sintonizable.

Área de la Ciencia:

Química supramolecular
Ingeniería de Cristal
Química orgánica

Sus antecedentes:

Los derivados del resorcinareno son plataformas versátiles para construir arquitecturas moleculares complejas.
El enlace halógeno (XB) es una poderosa interacción no covalente para dirigir el autoensamblaje.
El control de la arquitectura supramolecular a través de modificaciones estructurales sutiles sigue siendo un desafío clave.

Objetivo del estudio:

Investigar la formación de diversas arquitecturas supramoleculares utilizando bromuros de N-alquilo amonio resorcinareno y 1,4-diodoctafluorobutano.
Explorar el papel de los sustituyentes de las llantas superiores en el comportamiento de autoensamblaje.
Caracterizar las estructuras resultantes mediante métodos espectroscópicos y cristalográficos.

Principales métodos:

Síntesis de bromuros de N-alquilo amonio y resorcinareno.
Cocristalización con el 1,4-diodoctafluorobutano.
Análisis del estado de solución mediante espectroscopia de resonancia magnética nuclear (RMN).
Determinación estructural en estado sólido mediante cristalografía de rayos X.

Principales resultados:

Los sustituyentes de N-benzil obtuvieron conjuntos de mancuernas diméricas con huéspedes encapsulados.
Los grupos N-hexilo formaron pseudocápsulas poliméricas inducidas por XB y cápsulas diméricas que contienen 1,4-dioxano.
Los grupos N-propilo y N-ciclohexilo condujeron a cavitandos de cavidad profunda que exhibían autoinclusión y formaban redes supramoleculares en forma de caja de huevo 3D.

Conclusiones:

El estudio demuestra el impacto significativo de los sustituyentes del borde superior en la dirección del ensamblaje supramolecular a través del enlace halógeno.
Se puede lograr la formación sintonizable de diversas arquitecturas, incluidas cápsulas y redes 3D.
Estos hallazgos ofrecen información sobre el diseño racional de materiales supramoleculares funcionales.

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