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Las jaulas inherentemente quirales a través de la desimetrización jerárquica

Hao Zhou^1,2, Yu-Fei Ao^1,2, De-Xian Wang^1,2

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

|September 7, 2022

Resumen

Los investigadores crearon nuevas jaulas moleculares quirales con estructuras únicas. Estas jaulas demuestran una unión selectiva a los aniones quirales, allanando el camino para aplicaciones avanzadas de reconocimiento molecular.

Área de la Ciencia:

Química supramolecular
Síntesis orgánica
Estudios de la quiralidad

Sus antecedentes:

Las jaulas moleculares son cruciales para el reconocimiento molecular y la encapsulación.
El logro de la quiralidad inherente en las estructuras de la jaula presenta desafíos sintéticos.
La desimetrización jerárquica ofrece un camino hacia arquitecturas quirales complejas.

Objetivo del estudio:

Para sintetizar nuevas jaulas moleculares C1-simétricas inherentemente quirales.
Para investigar las propiedades de unión anión-π de estas jaulas quirales.
Establecer un método para acceder a las jaulas quirales enantiopuras en una escala de gramos.

Principales métodos:

Desimetrización jerárquica de una jaula tipo prisma D3.
Reacciones de sustitución progresiva que utilizan diferentes nucleófilos.
Cromatografía quiral para la resolución enantiomérica.
Cristalografía de rayos X para la determinación de la configuración absoluta.

Principales resultados:

Sintetizó con éxito jaulas inherentemente quirales C1-simétricas (C3 y C4) con diversidad estructural.
Producción a escala de gramos de jaulas enantiopuras obtenidas mediante cromatografía quiral.
Se ha demostrado la unión regio y enantioselectiva del anión-π con los aniones quirales de fosfato.
Cage (-) -C3a mostró una unión preferente a (S) -CPA- a través de interacciones sinérgicas anión-π.

Conclusiones:

La desimetrización jerárquica es una estrategia efectiva para crear jaulas inherentemente quirales.
Las jaulas quirales sintetizadas muestran una significativa selectividad quiral en la unión de aniones.
Estos hallazgos abren nuevas vías para el diseño de receptores quirales para el reconocimiento de aniones.

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