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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Expansión de la jaula de los fullerenos

Sheng Zhang¹, Yoshifumi Hashikawa¹, Yasujiro Murata¹

¹Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.

Journal of the American Chemical Society

|July 29, 2021

Resumen

Los investigadores desarrollaron un nuevo método para expandir químicamente las jaulas de fullereno, creando nuevas estructuras que contienen nitrógeno como C65N y C75N. Este avance permite la síntesis de fullerenos más grandes y funcionales para aplicaciones avanzadas.

Área de la Ciencia:

Química de los fullerenos
Química supramolecular
Síntesis orgánica

Sus antecedentes:

La expansión química de los fullerenos sigue siendo un desafío importante.
Los métodos anteriores para la modificación de la jaula de fullereno son limitados.

Objetivo del estudio:

Desarrollar un método eficiente para expandir las jaulas de fullereno.
Para sintetizar nuevas estructuras de fullereno que contienen nitrógeno.
Investigar las propiedades de los derivados endodérmicos del fullereno.

Principales métodos:

Síntesis en dos pasos que incluye triazina y N-fenilmaleimida.
La inclusión de una unidad C5N en jaulas de fullereno.
Síntesis de jaulas endodérmicas C75N con moléculas encapsuladas.

Principales resultados:

Expansión exitosa de las jaulas [60] y [70] de fullereno para formar C65N y C75N con heptágonos doblemente fusionados.
Orientación preferida demostrada del H2O encapsulado en la jaula C75N.
Interacción dipolar magnética revelada a través del espacio entre el H2 encapsulado y el átomo de nitrógeno.

Conclusiones:

La metodología desarrollada proporciona una ruta eficiente a los fullerenos expandidos que contienen nitrógeno.
Los estudios de encapsulación endohedral revelan interacciones moleculares únicas dentro de las jaulas expandidas.
Los hallazgos abren nuevas vías para la funcionalización del fullereno y la química supramolecular.

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