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Updated: Dec 7, 2025

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Floro N-confundido expandido: una plataforma para un sistema de anillos policíclicos de fusión múltiple a través de

Chengjie Li¹, Qizhao Li¹, Jiewei Shao¹

¹Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China.

Journal of the American Chemical Society

|September 28, 2020

Resumen

Los investigadores sintetizaron nuevos macrociclos a partir de porfirinoides expandidos, revelando una reactividad única. Estos compuestos, florinas e isoporfirinas, exhiben absorción en el infrarrojo cercano y sufren diversas transformaciones, ofreciendo nuevos marcos conjugados π.

Área de la Ciencia:

Química orgánica
Ciencias de los materiales
Química supramolecular

Sus antecedentes:

Los porfirinoides expandidos ofrecen propiedades electrónicas y estructurales únicas.
Las florinas y las isoporfirinas son análogos específicos de la porfirina con una fracción de metileno meso-sp3.
Estos compuestos exhiben una absorción extendida en el infrarrojo cercano (NIR).

Objetivo del estudio:

Para sintetizar nuevos macrociclos conjugados con π interrumpidos a partir de porfirinoides expandidos.
Para investigar la reactividad única de estos compuestos sintetizados.
Explorar su potencial para crear nuevos materiales absorbentes de NIR.

Principales métodos:

Síntesis de un análogo de floro pentapirrólico expandido con N-confuso 1.
Reacciones de oxidación con el 2,3-dicloro-5,6-diciano-p-benzoquinona y el azul mágico.
Estudios de coordinación de los metales con Pd (II).
Reacciones de reducción utilizando NaBH4.

Principales resultados:

El análogo 1 posee un sistema conjugado de π interrumpido con un HOMO más alto y un LUMO más bajo.
La oxidación produjo transformaciones estructurales en especies similares a la isoporfirina y un producto hexacíclico con puente de espiro-carbono.
La pentafirina aromática N-confundida se obtuvo a través de la migración del grupo fenilo.
La complejación Pd (II) condujo a un complejo bimetálico a través de la mesooxigenación.
La reducción dio lugar a la sustitución de hidrógeno nucleófilo regioselectiva.

Conclusiones:

Desarrolló un enfoque práctico para sintetizar nuevos marcos interrumpidos o aromáticos conjugados con π.
Se demostró la reactividad diversa de los macrociclos derivados de porfirinoides expandidos.
Destacó el potencial de estos marcos para aplicaciones que requieren la absorción de NIR.

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