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Los foldameres a base de indolocarbazoles son capaces de unirse a los haluros en el agua

Jae-Min Suk¹, Kyu-Sung Jeong

¹Center for Bioactive Molecular Hybrids, Department of Chemistry, Yonsei University, Seoul, 120-749, S. Korea.

Journal of the American Chemical Society

|August 15, 2008

Resumen

Los foldameres de indolocarbazoles forman estructuras helicoidales capaces de unir aniones a través de enlaces de hidrógeno. Su selectividad para aniones como el cloruro y el fluoruro cambia entre los disolventes acuosos y los orgánicos.

Área de la Ciencia:

Química supramolecular de las moléculas.
Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

Los foldameros son oligómeros sintéticos que imitan las estructuras secundarias de las proteínas.
Los andamios de indolocarbazoles ofrecen propiedades electrónicas y estructurales únicas para el reconocimiento molecular.

Objetivo del estudio:

Para sintetizar y caracterizar nuevos foldamers basados en indolocarbazol.
Para investigar las capacidades de unión aniónica de estos foldameres.
Para explorar la influencia del entorno del disolvente en la selectividad de unión de aniones.

Principales métodos:

Síntesis química de los foldameros del indolocarbazole.
Modelado computacional para la predicción estructural.
Espectroscopia de Resonancia Magnética Nuclear (RMN) (1H RMN, 2D ROESY) para el esclarecimiento estructural.
Estudios de unión de aniones en varios sistemas de disolventes.

Principales resultados:

Se han sintetizado con éxito foldameres indolocarbazoles que adoptan una conformación helicoidal.
Se ha demostrado la unión de aniones a través de enlaces de hidrógeno dentro de la cavidad helicoidal.
Se observa la unión selectiva de pequeños aniones hidrófilos (Cl- > F- > Br-) en el agua.
Se han reportado afinidades de unión inversa para F- y Cl- en una mezcla DMSO/MeOH, atribuidas a los efectos de solvación.

Conclusiones:

Los foldameros de indolocarbazoles son andamios efectivos para el reconocimiento de aniones.
La estructura helicoidal facilita la unión de aniones a través de la unión de hidrógeno.
La polaridad del disolvente y la energía de solvación tienen un impacto significativo en la selectividad de unión de aniones, destacando la naturaleza sintonizable de estos sistemas.

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