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El engranaje de quiralidad en una jaula achiral a través de la unión adaptativa
Qi-Ping Hu1,2, Hao Zhou1,2, Teng-Yu Huang1,2
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
|March 29, 2022
Resumen
Los investigadores desarrollaron una jaula molecular adaptativa que ata a los huéspedes y cambia de forma. Este huésped achiral induce con éxito la quiralidad en los huéspedes, ofreciendo un nuevo modelo para estudiar la inducción y discriminación quirales.
Área de la Ciencia:
- Química supramolecular
- Química orgánica
- Reconocimiento molecular
Sus antecedentes:
- Las jaulas moleculares son cruciales para la química huésped-huésped, permitiendo la unión selectiva y la encapsulación.
- Los huéspedes aquirales capaces de inducir la quiralidad en los huéspedes son raros y valiosos para la síntesis asimétrica.
- Comprender los cambios conformacionales en la unión del huésped es clave para diseñar sistemas supramoleculares funcionales.
Objetivo del estudio:
- Para sintetizar y caracterizar una jaula molecular trithiourea adaptativa.
- Para investigar la dinámica conformacional de la jaula y la estereodinámica al unirse a los aniones tricarboxilatos.
- Para explorar el potencial de la inducción quiral usando este sistema anfitrión flexible y achiral.
Principales métodos:
- Síntesis orgánica en varios pasos para la construcción de jaulas.
- Técnicas espectroscópicas (NMR, UV-Vis) para la caracterización y los estudios de unión.
- Cristalografía para determinar estructuras complejas y cambios conformacionales.
Principales resultados:
- Se sintetizó una nueva jaula molecular de trithiourea achiral con un rendimiento del 44%.
- La jaula forma un complejo de inclusión tipo sándwich con tricarboxilato de 1,3,5-benceno de alta afinidad (10^6 M^-1).
- La incorporación de huéspedes induce un bloqueo conformacional en la jaula, y los huéspedes quirales conducen a complejos similares a engranajes con sentido helicoidal definido, lo que demuestra la inducción quiral.
Conclusiones:
- La jaula molecular desarrollada es un huésped flexible y achiral capaz de una fuerte unión al huésped y una adaptación conformacional.
- Este sistema representa un raro ejemplo de inducción quiral por un huésped achiral, lo que permite estudios desacoplados de generación de racemato y discriminación quiral.
- Los hallazgos ofrecen una nueva plataforma para diseñar máquinas y sensores moleculares sofisticados.
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