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Síntesis de macrociclos aromáticos altamente retorcidos y no planos habilitados por un bloque de construcción de

Yuanming Li¹, Akiko Yagi², Kenichiro Itami^1,2,3

¹Institute of Transformative Bio-Molecules (WPI-ITbM) , Nagoya University , Chikusa, Nagoya 464-8602 , Japan.

Journal of the American Chemical Society

|January 28, 2020

Resumen

Los investigadores sintetizaron macrociclos aromáticos muy retorcidos utilizando el acoplamiento Suzuki-Miyaura. Estas nuevas estructuras exhiben propiedades fotofísicas únicas, incluida la emisión inducida por agregación y el solvatofluorocromismo, con una alta estabilidad.

Área de la Ciencia:

Química orgánica
Química supramolecular
Ciencias de los materiales

Sus antecedentes:

Los macrociclos aromáticos son cruciales en la química supramolecular.
El diseño de macrociclos no planos con ángulos de giro controlados sigue siendo un desafío.
La exploración de las relaciones estructura-propiedad en sistemas retorcidos es clave para los nuevos materiales.

Objetivo del estudio:

Para sintetizar nuevos macrociclos aromáticos no planos y muy retorcidos.
Investigar el impacto de la estructura molecular en las propiedades fotofísicas.
Establecer una ruta sintética versátil para arquitecturas macrocíclicas sintonizables.

Principales métodos:

Utilizó una reacción de acoplamiento Suzuki-Miyaura cuádruple.
Se empleó un nuevo bloque de construcción axialmente quiral no plano (4,5-bisarilfenantreno).
Se han variado sistemáticamente los socios de acoplamiento para modificar los espaciadores de macrociclos.

Principales resultados:

Se ha sintetizado con éxito una familia de macrociclos con ángulos de giro de aproximadamente 90°.
Desarrolló un emisor único de emisiones inducidas por agregación macrocíclica (AIE).
Se ha observado un notable solvatofluorocromismo en un macrociclo incorporado con naftalimida.
Se logra una resolución enantiomérica completa debido a la alta estabilidad conformacional.

Conclusiones:

La estrategia sintética desarrollada es efectiva para crear macrociclos retorcidos.
La modificación del espaciador influye significativamente en la forma del macrociclo y el comportamiento fotofísico.
Estos macrociclos estables y retorcidos son prometedores para materiales ópticos avanzados y aplicaciones quirales.

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