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Calix[n]azanediyldibenzoate: Síntesis asistida por enlace de hidrógeno intramolecular, acidichromismo y

Shuo Li¹, Zhihao Lu¹, Shuo Yan¹

¹School of Pharmaceutical and Chemical Engineering and Institute for Advanced Studies, Taizhou University, 1139 Shifu Road, Taizhou, Zhejiang 318000, China.

Organic letters

|September 5, 2025

Resumen

Los enlaces de hidrógeno intramoleculares crean arenas macrocíclicas rígidas por primera vez. Estos nuevos macrociclos muestran respuestas acidocrómicas rápidas y permiten el ensamblaje orientado de aldehídos.

Área de la Ciencia:

Química supramolecular
Síntesis orgánica
Ciencias de los materiales

Sus antecedentes:

Los enlaces de hidrógeno intramoleculares (IMHB) pueden inducir rigidez estructural.
Las arenas macrocíclicas son andamios importantes en la química supramolecular.
Los materiales sensibles al estímulo son cruciales para las aplicaciones avanzadas.

Objetivo del estudio:

Para sintetizar nuevas arenas macrocíclicas utilizando la rigidez inducida por el IMHB.
Investigar las propiedades acidocrómicas de los macrociclos sintetizados.
Explorar el potencial de estos macrociclos en el ensamblaje orientado.

Principales métodos:

Reacción de condensación en un solo paso del dimetilo 2,2'-azandioldibenzoato y el paraformaldehído.
Síntesis de calix[n]azandilibenzoatos (C[n]A, n=3, 4, 5).
Análisis de la respuesta acidocrómica y determinación de la estructura cristalina.

Principales resultados:

Síntesis exitosa de los macrociclos C[n]A.
Se ha mostrado una respuesta acidocrómica rápida y significativa debido a la transferencia de carga intramolecular.
El conformador C[4]A se autoensambló en canales 1D para el ensamblaje de aldehído orientado.

Conclusiones:

La rigidez inducida por IMHB es una estrategia novedosa para la síntesis de arenos macrocíclicos.
Los macrociclos sintetizados son candidatos prometedores para materiales sensibles al estímulo.
Demostró un nuevo método para controlar la orientación del cristal y el ensamblaje molecular.

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