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Formación de triple hélice en discotecas anfifílicas: desmitificando los efectos del disolvente en el autoensamblaje
Martijn A J Gillissen1, Marcel M E Koenigs, Jolanda J H Spiering
1Institute of Complex Molecular Systems, Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology , P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
Journal of the American Chemical Society
|December 10, 2013
Resumen
Las moléculas discóticas quirales, anfifílicas se autoensamblan en fibras supramoleculares. La presencia de agua induce la agrupación de fibras, lo que demuestra un vínculo entre el autoensamblaje molecular y la termodinámica del disolvente.
Área de la Ciencia:
- Química supramolecular de las moléculas.
- Ciencia de los materiales Ciencia de los materiales.
- Química orgánica es la química orgánica.
Sus antecedentes:
- Las moléculas discóticas son conocidas por su autoensamblaje en estructuras ordenadas.
- La anfifilicidad es una propiedad clave para controlar el autoensamblaje en solución.
- Los motivos de benceno-1,3,5-tricarboxamida (BTA) ofrecen una plataforma versátil para el diseño de moléculas funcionales.
Objetivo del estudio:
- Para sintetizar y caracterizar nuevas moléculas quirales, anfifílicas y discoticas.
- Para investigar el comportamiento de autoensamblaje de estas moléculas en mezclas de agua y alcohol.
- Para explorar la influencia de la composición del disolvente y la temperatura en las estructuras supramoleculares.
Principales métodos:
- Síntesis de derivados de benceno-1,3,5-tricarboxamida (BiPy-BTA) sustituidos por 3,3'-bis-acylamino) -2,2'-bipiridina y sus derivados.
- Diseminación de rayos X de ángulo pequeño (SAXS) para el análisis estructural.
- Microscopía electrónica de transmisión criogénica (Cryo-TEM) para visualizar estructuras autoensambladas.
- Espectroscopia de dicroísmo circular (CD) para evaluar la quiralidad y las transiciones estructurales.
Principales resultados:
- Preparó con éxito moléculas discóticas quirales, anfifílicas con grupos periféricos asimétricos.
- Autoensamblaje observado en fibras supramoleculares con una o tres moléculas en sección transversal.
- Se demostró que la adición de agua induce la agrupación de estas fibras supramoleculares.
- Se identificó una correlación entre el comportamiento de fase y la termodinámica de las mezclas de agua y alcohol.
Conclusiones:
- Las moléculas BiPy-BTA diseñadas exhiben un autoensamblaje controlado en arquitecturas supramoleculares ordenadas.
- La naturaleza anfifílica y la quiralidad son cruciales para la formación y agrupación de fibras observadas.
- El estudio pone de relieve la intrincada relación entre las propiedades del disolvente y el autoensamblaje supramolecular.
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