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Macrociclizaciones de un solo paso altamente eficientes asistidas por el plegamiento y la preorganización de
Lihua Yuan1, Wen Feng, Kazuhiro Yamato
1Department of Chemistry, Natural Sciences Complex, University at Buffalo, The State University of New York, Buffalo, New York 14260, USA.
Journal of the American Chemical Society
|September 10, 2004
Resumen
Los investigadores desarrollaron un método novedoso de un solo paso para sintetizar hexa (aramidas) macrocíclicas con altos rendimientos. Este enfoque utiliza la preorganización de la columna vertebral a través de enlaces de hidrógeno en los foldamers, simplificando los procesos de macrociclado.
Área de la Ciencia:
- Química de Polímeros La Química de Polímeros es la química de los polímeros.
- Síntesis orgánica La síntesis orgánica.
- Química supramolecular de las moléculas.
Sus antecedentes:
- Los métodos tradicionales de macrociclado a menudo sufren de bajos rendimientos y requieren una alta dilución.
- Lograr una síntesis eficiente de polímeros macrocíclicos como las hexa (arámides) sigue siendo un desafío.
Objetivo del estudio:
- Desarrollar un método de macrociclado de un solo paso y altamente eficiente para las hexa-aramidas.
- Demostrar la utilidad de la preorganización de la columna vertebral a través de la unión de hidrógeno en los foldameres para la macrociclado controlado.
Principales métodos:
- Diseño y síntesis de precursores de foldamer rigidificados en la columna vertebral con enlaces de hidrógeno localizados de tres centros.
- Reacción de macrociclado de un solo paso entre un cloruro de diacido y una diamina.
- Análisis de las mezclas y productos de reacción utilizando la espectrometría de masas de desorción láser asistida por matriz / ionización-tiempo de vuelo (MALDI-TOF).
Principales resultados:
- Se han logrado macrociclaciones altamente eficientes de un solo paso que producen hexa (((aramidas macrocíclicas) en rendimientos del 69-82%.
- Demostrado que la preorganización de la columna vertebral, facilitada por enlaces de hidrógeno en los foldamers, promueve una macrociclado eficiente.
- Se obtienen hexámeres cíclicos como producto principal en diversas condiciones, a diferencia de los métodos tradicionales que requieren una alta dilución y producen un producto bajo.
Conclusiones:
- El enfoque de macrociclado de un solo paso descrito es general y altamente eficiente para sintetizar hexa-aramidas macrocíclicas.
- El diseño de Foldamer que incorpora la preorganización de enlaces de hidrógeno es una poderosa estrategia para superar las limitaciones en las reacciones de macrociclado.
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