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Un grupo funcional fotobásico

Jie He¹, Flora W Kimani¹, John C Jewett¹

¹Department of Chemistry and Biochemistry, University of Arizona, 1306 East University Boulevard, Tucson, Arizona 85721, United States.

Journal of the American Chemical Society

|July 28, 2015

Resumen

Los investigadores desarrollaron un triazabutadieno sensible a la luz que se vuelve básico cuando se expone a 350 nm de luz. Esta fotobasa puede ajustar el pH y catalizar reacciones, ofreciendo un nuevo control fotoquímico en la química orgánica.

Área de la Ciencia:

Química orgánica
La fotoquímica

Sus antecedentes:

El control de la reactividad química con la luz está establecido en la química orgánica.
La basicidad compuesta modulada con estímulos externos sigue siendo menos explorada.

Objetivo del estudio:

Desarrollar una base fotointercambiable para el control preciso de las reacciones químicas.
Demostrar la modulación de la basicidad inducida por la luz en un nuevo sistema de triazabutadieno.

Principales métodos:

Síntesis de un triazabutadieno soluble en agua y uno soluble en disolvente aprótico.
Fotoisomerización del triazabutadieno con luz de 350 nm.
Monitoreo de los cambios de pH en las soluciones acuosas y la basicidad en los disolventes orgánicos.
Catalización de una reacción de condensación utilizando la fotobasa.

Principales resultados:

Se sintetizó un derivado de triazabutadieno que exhibe una mayor basicidad tras la fotoisomerización.
El pH de las soluciones acuosas se ajustó con éxito utilizando luz de 350 nm.
Se observaron cambios de basicidad inducidos por la luz tanto en disolventes orgánicos acuosos como apróticos.
La fotobasa catalizó efectivamente una reacción de condensación modelo.

Conclusiones:

La fotoisomerización del triazabutadieno proporciona un nuevo método para la basicidad controlada por la luz.
Esta fotobasa ofrece una nueva herramienta para la síntesis fotoquímica y el control de la reacción.
La capacidad de sintonizar la basicidad con la luz abre caminos para transformaciones orgánicas avanzadas.

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