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Introducción al prisma[4]areno: un macrociclo con quiralidad inherente enantioméricamente resoluble y propiedades

Paolo Della Sala¹, Carmen Talotta¹, Margherita De Rosa¹

¹Laboratory of Supramolecular Chemistry, Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, Salerno, Italy.

Journal of the American Chemical Society

|June 4, 2025

Resumen

Los investigadores informan de los primeros prismarenos inherentemente quirales con enantiómeros resueltos. Estas moléculas únicas mantienen la quiralidad y muestran potencial para el reconocimiento enantioselectivo de huéspedes.

Área de la Ciencia:

Química supramolecular
Química orgánica
Estudios de la quiralidad

Sus antecedentes:

Los prismarenos son compuestos macrocíclicos con aplicaciones potenciales en el reconocimiento molecular.
El logro y la resolución de enantiómeros de macrociclos complejos sigue siendo un desafío sintético.
Comprender los factores que estabilizan la quiralidad en sistemas tensos es crucial.

Objetivo del estudio:

Para sintetizar y resolver los enantiómeros de un prismareno inherentemente quiral.
Investigar las propiedades quirópticas, incluida la luminiscencia polarizada circular (CPL).
Demostrar las capacidades de reconocimiento enantioselectivo de los prismarenos resueltos.

Principales métodos:

Síntesis de plantillas termodinámicas utilizando cationes selectivos.
Cromatografía líquida quiral de alto rendimiento (HPLC) para la resolución de enantiómeros.
Teoría funcional de densidad dependiente del tiempo (TDDFT) y espectroscopia ECD/UV-vis para la asignación de configuración.

Principales resultados:

Síntesis y resolución exitosas de enantiómeros de prisma[4]areno (PrS[4]iPe).
La estructura en estado sólido reveló cristales racémicos que forman cadenas poliméricas supramoleculares.
Se observaron propiedades significativas de CPL con una relación de disimetría de 0,008.
Se ha demostrado el reconocimiento enantioselectivo de huéspedes quirales de amonio.

Conclusiones:

Los prismarenos sintetizados exhiben una quiralidad inherente estable debido a las estructuras tensas.
Los enantiómeros resueltos poseen propiedades quirópticas distintas, incluida la CPL.
Estos prismarenos quirales son candidatos prometedores para la química anfitrión-invitado enantioselectiva.

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