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Tetrasubstituido planar quiral [2.2]paraciclófano: resolución óptica y funcionalización

Yasuhiro Morisaki¹, Masayuki Gon, Takahiro Sasamori

¹Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University Katsura , Nishikyo-ku, Kyoto 615-8510, Japan.

Journal of the American Chemical Society

|February 18, 2014

Resumen

Los investigadores sintetizaron macrociclos ópticamente activos en forma de hélice a partir de bloques de construcción de ciclófanos quirales planas. Estos compuestos exhiben excelentes propiedades quirópticas, incluyendo alta fluorescencia y luminiscencia circularmente polarizada.

Área de la Ciencia:

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

Sus antecedentes:

Los ciclofanos quirales son valiosos andamios en la síntesis asimétrica y en la ciencia de los materiales.
Desarrollar métodos eficientes para acceder a los derivados de ciclófano ópticamente puros sigue siendo un desafío.

Objetivo del estudio:

Para lograr la resolución óptica de los tetrasubstituidos [2.2] paraciclophanes.
Para sintetizar nuevos compuestos macrocíclicos en forma de hélice con núcleos ciclófanos quirales planas.
Para investigar las propiedades quirópticas de los macrociclos sintetizados.

Principales métodos:

Resolución óptica de 4,7,12,15-tetrasubstituido por [2.2]paraciclofano.
Transformación química de los ciclofanos disueltos en bloques de construcción quirales planas.
Síntesis de compuestos macrocíclicos con forma de hélice que incorporan el núcleo quiral ciclófano.

Principales resultados:

Resolución óptica exitosa del derivado ciclófano objetivo.
Síntesis de compuestos macrocíclicos ópticamente activos con un núcleo ciclófano quiral planar.
Demostración de excelentes propiedades quirópticas, incluida la alta eficiencia cuántica de fluorescencia.
Observación de un gran factor de disimetría de luminiscencia polarizado circularmente.

Conclusiones:

El método desarrollado proporciona acceso a valiosos bloques de construcción de ciclófano quiral planar.
Los macrociclos sintetizados exhiben características prometedoras para aplicaciones en reconocimiento quiral y optoelectrónica.
Este trabajo amplía el alcance de los compuestos quirales macrocíclicos con propiedades fotofísicas únicas.

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