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Smaragdyrins de una y dos formas
Yutao Rao1, Wenjing Zhou1, Ling Xu1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine, Ministry of Educational of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha 410081 , P. R. China.
Journal of the American Chemical Society
|November 7, 2019
Resumen
Los investigadores sintetizaron mutantes estables de smaragdyrina neo-confundidos y sus bases libres, revelando propiedades únicas como la diprotonación y oxigenación regioselectivas. Estos hallazgos avanzan en el estudio de las porfirinas expandidas.
Área de la Ciencia:
- Química orgánica
- Química de las porfirinas
- Química supramolecular
Sus antecedentes:
- Las esmaragdirinas son porfirinas expandidas importantes pero desafiantes.
- Recientemente se ha logrado una síntesis anterior de esmaragdirinas.
- Los porfirinoides neoconfusos ofrecen propiedades electrónicas y estructurales únicas.
Objetivo del estudio:
- Para sintetizar nuevos complejos de BF2 de esmeraldina mono y doblemente confundidos.
- Para obtener las correspondientes bases libres de esmaragdirina [22] neoconfusa.
- Investigar las propiedades características y la reactividad de estos nuevos compuestos.
Principales métodos:
- Reacciones de sustitución nucleófila entre una dibromodipirrina y tripiranos N-confundidos.
- Demetalación con ácido metanesulfónico para obtener bases libres.
- Reacciones de oxigenación y desmetalización para una mayor funcionalidad.
Principales resultados:
- Síntesis exitosa de complejos de BF2 de esmaragdirina [22] aislados y doblemente confundidos.
- Aislamiento de las bases libres de esmeragdirina [22] neoconfusa sensibles al aire.
- Observación de la disminución de la corriente de anillo diatrópica, la diprotonación regioselectiva y la oxigenación suave.
Conclusiones:
- Se sintetizaron mutantes estables de esmeraldina y sus bases libres.
- Estos compuestos exhiben propiedades únicas que incluyen protonación y oxigenación regioselectivas.
- El estudio proporciona acceso a nuevos porfirinoides expandidos para su posterior investigación.
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