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Transferencia intramolecular de protones de estado excitado de anilinio a azonio en un andamio catiónico que exhibe

Dibyajyoti Pathak¹, Nyaya Prakash Pradhan¹, Naresh Aggarwal²

¹Department of Chemistry Indian, Institute of Science Education and Research Bhopal (IISER Bhopal), Bypass Road, Bhauri, Bhopal, Madhya Pradesh 462066, India.

The journal of physical chemistry. A

|August 21, 2025

Resumen

Diseñamos un nuevo andamio de diaminoazobenzeno que exhibe transferencia intramolecular de protones en estado excitado (ESIPT) con doble emisión sintonizable. Este andamio muestra potencial para aplicaciones fotofísicas avanzadas.

Área de la Ciencia:

Química fotofísica
Química orgánica
Ciencias de los materiales

Sus antecedentes:

La transferencia intramolecular de protones en estado excitado (ESIPT) es crucial para los fluoróforos orgánicos, ya que ofrece grandes cambios de Stokes y una emisión sintonizable.
Los materiales basados en ESIPT son valiosos para diversas aplicaciones ópticas y de detección.

Objetivo del estudio:

Diseñar y caracterizar un nuevo andamio activo para el ESIPT, el diaminoazobenzeno.TFA (DAB.TFA).
Investigar el mecanismo ESIPT tipo anilinio-azonio (Ano-Azo) y sus propiedades fotofísicas.
Explorar métodos para controlar el perfil de emisiones del andamio diseñado.

Principales métodos:

Síntesis y caracterización del andamio DAB.TFA.
Mediciones fotofísicas, incluida la espectroscopia de estado estacionario y de resolución temporal (espectroscopia de absorción transitoria).
Investigaciones computacionales para confirmar el proceso del ESIPT.

Principales resultados:

DAB.TFA exhibe ESIPT de tipo anilinio a azonio (Ano-Azo), estabilizado por enlaces de hidrógeno intramoleculares.
Se observó un gran desplazamiento de Stokes de 6474 cm-1, junto con una doble emisión ratiométrica dependiente de la excitación.
Los perfiles de emisión eran ajustables a través de la sustitución isotópica y la acidez del agente protonante, con tiempos de vida en estado excitado de 1,5 ps (ESA) y 0,6 ps (SE).

Conclusiones:

El andamio DAB.TFA diseñado demuestra con éxito el ESIPT con propiedades fotofísicas controlables.
El estudio pone de relieve el potencial de los sistemas Ano-Azo ESIPT para aplicaciones que requieren emisiones ajustables y grandes turnos de Stokes.
Las investigaciones adicionales pueden explorar modificaciones para mejorar las emisiones y las aplicaciones específicas.

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