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Síntesis no covalente de hexámeros cíclicos de forma persistente a partir de sintones supramoleculares basados en

Yong Yang¹, Min Xue, Jun-Feng Xiang

¹Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Journal of the American Chemical Society

|August 19, 2009

Resumen

Los sintones de hidrazida ditópica se autoensamblan en hexámeres cíclicos estables y de forma persistente. Los grupos terminativos influyen en la estabilidad del ensamblaje y pueden inducir la quiralidad supramolecular en solución.

Área de la Ciencia:

Química supramolecular de las moléculas.
Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

El autoensamblaje es un proceso fundamental en química y biología.
Diseñar moléculas que formen estructuras supramoleculares específicas de manera confiable es un desafío clave.
Los motivos de hidrazida ofrecen capacidades únicas de enlace de hidrógeno para el reconocimiento molecular.

Objetivo del estudio:

Para investigar el autoensamblaje de sintones supramoleculares basados en hidrazida ditópica unidos por espaciador de 120 grados.
Explorar la influencia de los grupos terminativos en la estabilidad y propiedades de los conjuntos resultantes.
Para demostrar la formación de hexámeres cíclicos de forma persistente y su quiralidad supramolecular.

Principales métodos:

Síntesis de sintones supramoleculares basados en hidrazida ditópica con diferentes grupos terminativos.
Caracterización del autoensamblaje en disolventes de enlace de hidrógeno apolares y competitivos utilizando espectroscopia de Resonancia Magnética Nuclear (RMN).
Análisis de la estabilidad del ensamblaje y la quiralidad supramolecular utilizando espectroscopia de dicroísmo circular (CD).

Principales resultados:

Se han formado exitosamente hexámeres cíclicos de forma persistente a partir de sintones de hidrazida ditópica en disolventes apolares.
Los estudios de RMN confirmaron conformaciones entrelazadas en disolventes apolares y ejes C2 en DMSO-d6).
Los grupos terminativos tuvieron un impacto significativo en la estabilidad del ensamblaje, y los grupos ureido-hidrazida produjeron los hexámeres más estables.
Los grupos terminativos auxiliares quirales indujeron una quiralidad supramolecular observable en solución.

Conclusiones:

Las sintonas de hidrazida ditópica son bloques de construcción efectivos para crear hexámeres cíclicos de forma persistente.
La estabilidad y las propiedades de estos conjuntos supramoleculares se pueden ajustar con precisión mediante la modificación de grupos terminativos.
La quiralidad supramolecular demostrada abre posibilidades para materiales quirales y aplicaciones de detección.

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