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Desde cadenas abiertas plegables hasta macrociclos de forma persistente: síntesis, impacto en el ordenamiento 2D y
Soobin Kim1, Henry D Castillo2, Milim Lee1
1Department of Chemistry , Seoul National University , 1 Gwanak-ro, Gwanak-gu, Seoul 08826 , Korea.
Journal of the American Chemical Society
|March 15, 2018
Resumen
Diseñamos moléculas de bis (triazol) benceno para su autoensamblaje en la superficie. La estructura molecular variable y los grupos periféricos controlan con precisión el ordenamiento de la película orgánica y la respuesta a los estímulos.
Área de la Ciencia:
- Ciencias de los materiales
- Química supramolecular
- Productos electrónicos orgánicos
Sus antecedentes:
- El autoensamblaje de moléculas pequeñas es clave para las películas orgánicas ordenadas en aplicaciones químicas y electrónicas.
- El control preciso de las interacciones intermoleculares es crucial para programar la estructura y la función molecular.
- Las moléculas basadas en bis (triazol) benceno ofrecen una plataforma sintonizable para estudios de autoensamblaje en la superficie.
Objetivo del estudio:
- Diseñar y sintetizar nuevas moléculas conjugadas π basadas en bis (triazol) benceno.
- Investigar el comportamiento de autoensamblaje dependiente de la estructura de estas moléculas en las superficies.
- Explorar la influencia de la estructura molecular y los grupos periféricos en el ordenamiento de la superficie y la respuesta a los estímulos.
Principales métodos:
- Síntesis de derivados de bis (triazol) benceno mediante acoplamiento cruzado C-C en etapa tardía.
- Microscopía de túnel de barrido (STM) para analizar el autoensamblaje molecular en las superficies.
- Estudios comparativos de precursores lineales y macrociclos ciclizados con diferentes grupos periféricos (alquilo frente al oligoetilenglicol).
Principales resultados:
- Se observaron comportamientos distintos de autoensamblaje basados en la flexibilidad de la columna vertebral molecular y la química del grupo periférico.
- Las cadenas de alquilo promovieron estructuras interdigitadas, mientras que las cadenas de oligoetilenglicol (OEG) condujeron a núcleos π más densos.
- Los macrociclos ciclizados mostraron una cinética de autoensamblaje más rápida que los precursores lineales debido a la libertad de conformación restringida.
- La perturbación de la punta del STM y las cosolutas afectaron significativamente la cinética del autoensamblaje y el patrón de la superficie.
Conclusiones:
- El diseño molecular, incluida la restricción conformacional y la selección de grupos periféricos, permite un control preciso sobre el autoensamblaje de la superficie.
- Las interacciones no covalentes débiles en solución pueden amplificarse para moléculas confinadas en superficies 2D, lo que lleva a un ordenamiento robusto.
- Estos hallazgos proporcionan información sobre la programación de interacciones moleculares para materiales orgánicos avanzados y patrones de superficie.
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