Síntesis y caracterización de 4-(4-etinilfenil)-2,2’bipiridna para funcionalización de complejos de Renio (I) tricarbonil
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Fecha
2021
Profesor/a Guía
Facultad/escuela
Idioma
es
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Universidad Andrés Bello
Nombre de Curso
Licencia CC
Licencia CC
Resumen
Los complejos de renio (I) tricarbonil diimina han jugado un rol importante en la innovación de
compuestos organometálicos enfocados a su aplicación en la biología, ya que, los compuestos
obtenidos mediante síntesis pueden ser funcionalizados a moléculas con actividad biológica
(proteínas, azucares, ADN, etc.), las cuales son utilizadas para dirigir los complejos a lugares
específicos dentro de los medios biológicos. El objetivo de esta metodología es desarrollar
aplicaciones como captura de imágenes celulares colocalizadas de alta resolución mediante la
luminiscencia que presentan estos complejos o aprovechar su potencial citotóxico frente a células
cancerígenas entre algunas posibilidades
La funcionalización de los complejos de renio (I) tricarbonil con moléculas con actividad biológica
se realiza generalmente a través de los ligandos orgánicos que acompañan al metal central, los
cuales son generalmente derivados de diiminas. Estos compuestos N-heterocíclicos pueden ser
funcionalizados mediante reacciones orgánicas que permiten obtener diiminas mono-sustituidas
con grupos reactivos. Una ruta sintética simple para obtener estas uniones es utilizando chalconas
como precursores. Estos compuestos tienen la ventaja de tener bajos costos de síntesis y pueden
ser utilizados para formar aductos de Diels-Alder, los cuales pueden derivarse para obtener
bipiridinas mono-sustituidas.
En esta unidad se presenta la síntesis de la bipiridina mono-sustituida 4-(4-etinilfenil)-2,2’-
bipiridina, a partir de una chalcona, con el fin de conseguir bipiridinas con potencialidad de unirse
tanto a centros metálicos para formar complejos o bien, en simultáneo a moléculas con actividad
biológica que permitan ampliar las aplicaciones de complejos organometálicos como los
complejos de renio (I) tricarbonílico. Además, en este trabajo se incluye la síntesis y
caracterización de un complejo de renio que posee un ligante bipiridina.
Rhenium (I) diimine tricarbonyl complexes have presented an important role in the innovation of organometallic compounds focused on biology, due to the compounds obtained by synthesis, can be functionalized to molecules with specific biological activity (proteins, sugars, DNA, etc), which are use to aim complexes to specific locations within biological environments. The goal of this methodology is to develop a complex capable of perform in applications such as cellular imaging thank to the luminescence presented by these complexes or taking advantage of their cytotoxic potential against cancer cells, among some other possibilities. The functionalization of the rhenium (I) tricarbonyl complexes to biologically active molecules is generally performed to the organic ligands that coordinate the central metal, which are generally derived from diimines. These N-heterocyclic compounds can be functionalized through organic reactions to obtain monosubstituted diimines with reactive groups. A simple synthetic route is using chalcones as precursors. These compounds have the advantage of having low synthesis costs and can be used to form Diels-Alder adducts, which can be used to produce monosubstituted bipyridines. This reasearch presents the synthesis of mono-substituted 4-(4-etinylphenyl)-2,2'-bipyridine, obtained from a chalcone, in order to obtain bipyridines ligands with the potential to coordinate metallic centers to form complexes or, simultaneously, to bind to molecules with biological activity. This allows the extension of the applications of organometallic complexes such as rhenium (I) tricarbonylic complexes. Moreover, this work includes the synthesis and characterization of a rhenium complex that has a bipyridine ligand
Rhenium (I) diimine tricarbonyl complexes have presented an important role in the innovation of organometallic compounds focused on biology, due to the compounds obtained by synthesis, can be functionalized to molecules with specific biological activity (proteins, sugars, DNA, etc), which are use to aim complexes to specific locations within biological environments. The goal of this methodology is to develop a complex capable of perform in applications such as cellular imaging thank to the luminescence presented by these complexes or taking advantage of their cytotoxic potential against cancer cells, among some other possibilities. The functionalization of the rhenium (I) tricarbonyl complexes to biologically active molecules is generally performed to the organic ligands that coordinate the central metal, which are generally derived from diimines. These N-heterocyclic compounds can be functionalized through organic reactions to obtain monosubstituted diimines with reactive groups. A simple synthetic route is using chalcones as precursors. These compounds have the advantage of having low synthesis costs and can be used to form Diels-Alder adducts, which can be used to produce monosubstituted bipyridines. This reasearch presents the synthesis of mono-substituted 4-(4-etinylphenyl)-2,2'-bipyridine, obtained from a chalcone, in order to obtain bipyridines ligands with the potential to coordinate metallic centers to form complexes or, simultaneously, to bind to molecules with biological activity. This allows the extension of the applications of organometallic complexes such as rhenium (I) tricarbonylic complexes. Moreover, this work includes the synthesis and characterization of a rhenium complex that has a bipyridine ligand
Notas
Unidad de Investigación (Licenciado en Química)
Proyecto Fondecyt iniciación 11140401 Proyecto interno DI-31-17/RG
Proyecto Fondecyt iniciación 11140401 Proyecto interno DI-31-17/RG
Palabras clave
Compuestos de Renio