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Hidrocarburos de Chichibabin funcionalizados con sulfones: Diradicaloides estables con transferencia de carga de

Zhibiao Zhou^1,2,3, Kun Yang^1,2, Long He^1,4

¹State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical EngineeringHunan University, Changsha 410082, China.

Journal of the American Chemical Society

|February 28, 2024

Resumen

Los investigadores desarrollaron diradicaloides orgánicos estables con grupos sulfónicos, logrando una emisión profunda en el infrarrojo cercano (NIR) más allá de los 900 nm. Este avance ofrece nuevas posibilidades para el diseño de materiales de capa abierta avanzados para aplicaciones NIR.

Área de la Ciencia:

Productos electrónicos orgánicos
Ciencias de los materiales
La fotofísica

Sus antecedentes:

Los diodos orgánicos emisores de luz (OLED) han avanzado con los emisores monorádicos.
Las propiedades de luminiscencia de los diradicaloides orgánicos siguen siendo poco exploradas.
La exploración de nuevas estructuras moleculares es crucial para los dispositivos optoelectrónicos de próxima generación.

Objetivo del estudio:

Sintetizar y caracterizar una nueva clase de diradicaloides estables de hidrocarburos de Chichibabin funcionalizados con sulfones.
Investigar el impacto de las variaciones de los sustituyentes en sus propiedades optoelectrónicas y magnéticas.
Explorar su potencial para la emisión de infrarrojos cercanos (NIR).

Principales métodos:

Se empleó una nueva estrategia de acoplamiento radical-radical para la síntesis.
Se utilizaron técnicas experimentales completas para la caracterización.
Se realizaron cálculos químicos cuánticos para comprender las relaciones estructura-propiedad.

Principales resultados:

Se han sintetizado con éxito diradicaloides estables (SD-1-3) con caracteres diradicales de 0,44-0,70.
Estos materiales exhiben una emisión NIR rara más allá de 900 nm, con un récord de 998 nm para SD-2.
Las variaciones de los sustituyentes (H/CF3/OMe) ajustaron significativamente las propiedades optoelectrónicas y magnéticas.

Conclusiones:

La incorporación del grupo sulfón rompe la simetría cuasi-C2, induciendo la transferencia de carga en estado excitado y la emisión profunda de NIR.
El derivado sustituido por CF3 (SD-2) muestra un gran desplazamiento de Stokes y la longitud de onda de emisión de radicales fluorescentes más larga reportada.
Este trabajo establece una nueva ruta sintética para los hidrocarburos de Chichibabin y permite el diseño de materiales de capa abierta emisores de NIR.

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