Trímeros de fosfacenos modificados con derivados de 2,2'-bifenildiol: síntesis y caracterización
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2015
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es
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Universidad Andrés Bello
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Licencia CC
Licencia CC
Resumen
Los fosfacenos son compuestos formados por enlaces simples y dobles
alternados entre átomos de fósforo y nitrógeno, donde el átomo de fósforo se
encuentra sustituido por dos grupos R (iguales o distintos). La naturaleza de los
sustituyentes les confieren propiedades físicas y químicas diversas. Esta unidad
se enmarca dentro de un proyecto mayor que tiene como finalidad obtener
nuevos materiales híbridos inorgánicos-orgánicos, donde el trímero de
fosfaceno es el componente inorgánico, mientras que los bifenoles
corresponden a la componente orgánica. Si se logra establecer una
metodología aplicable a los trímeros, ésta se podrá proyectar a futuro en
polímeros. En relación a los estudios previos de trímeros de ciclofosfacenos,
sustituidos con 2,2'-bifenildiol sin sustituyentes, podemos decir que han sido
ampliamente estudiados, en contraste, aquellos con sustituyentes no han sido
estudiados.
Durante esta Unidad de Investigación se ha logrado sintetizar los ligandos
orgánicos 3,3'-dinitro-2,2'-bifenildiol (2), el 3-nitro-2,2'-bifenildiol (3) y 5,5´-
dibromo-2,2'-bifenildiol (4), los que fueron caracterizados mediante IR, 1H y 13CRMN,
adicionalmente la estructura de los compuestos (3) y (4) fue determinada
difracción de Rayos X de monocristal. El compuesto 5,5'-dibromo-2,2'-bifenildiol
se utilizó para preparar nuevos trímeros de ciclofosfaceno sustituidos
obteniéndose como productos los compuestos 1,1-[5,5'-dibromo-1,1'-bifenilo-
2,2'-bisolato]-3,3,5,5-bis–[1,1'-bifenilo-2,2'-bisolato] ciclofosfaceno (6) y tris [5,5'-
dibromo-1,1'-bifenilo-2,2'-bisolato] ciclofosfaceno (7), tal como lo muestra la
Esquema 1.
Phosphazenes are inorganic compounds formed by alternated simple and double bonds between phosphorous and nitrogen atoms, phosphorous atoms substituted by two R groups. The nature of the substituents give them diverse chemical and physical properties. This work is part of a broader project that aims to obtain new inorganic-organic hybrid materials, where the phosphazene trimer is the inorganic component, while biphenyls correspond to the organic one. If we can establish a methodology for the trimers, it will be possible to project it in the future in polymers. In relation to the previously described cyclophosphazenes, in particular, those bearing 2,2´-biphenyldiol, they has been widely described in the literature in contrast the studies of those substituted are scare. During this work we were able to synthesize the organic ligands 3,3'-dinitro-2,2'- biphenyldiol (2), 3-nitro-2,2-biphenyldiol (3) and 5,5'-dibromo-2,2'-biphenyldiol (4), which were characterized by IR, 1H and 13C NMR, additionally for compounds (3) and (4) the single crystal X-ray diffraction was determined. The compound 5,5'-dibromo-2,2'-biphenyldiol was used to prepare new substituted cyclophosphazene trimers obtaining 1,1- [5,5'-dibromo-1,1'-biphenyl-2, 2'- bisolato] -3,3,5,5-bis- [1,1'-biphenyl-2,2'-bisolato] cyclophosphacene (6) and tris [5,5'-dibromo-1,1'-biphenyl-2,2'-bisolato] cyclophosphacene (7) as products, as shown in Scheme 1.
Phosphazenes are inorganic compounds formed by alternated simple and double bonds between phosphorous and nitrogen atoms, phosphorous atoms substituted by two R groups. The nature of the substituents give them diverse chemical and physical properties. This work is part of a broader project that aims to obtain new inorganic-organic hybrid materials, where the phosphazene trimer is the inorganic component, while biphenyls correspond to the organic one. If we can establish a methodology for the trimers, it will be possible to project it in the future in polymers. In relation to the previously described cyclophosphazenes, in particular, those bearing 2,2´-biphenyldiol, they has been widely described in the literature in contrast the studies of those substituted are scare. During this work we were able to synthesize the organic ligands 3,3'-dinitro-2,2'- biphenyldiol (2), 3-nitro-2,2-biphenyldiol (3) and 5,5'-dibromo-2,2'-biphenyldiol (4), which were characterized by IR, 1H and 13C NMR, additionally for compounds (3) and (4) the single crystal X-ray diffraction was determined. The compound 5,5'-dibromo-2,2'-biphenyldiol was used to prepare new substituted cyclophosphazene trimers obtaining 1,1- [5,5'-dibromo-1,1'-biphenyl-2, 2'- bisolato] -3,3,5,5-bis- [1,1'-biphenyl-2,2'-bisolato] cyclophosphacene (6) and tris [5,5'-dibromo-1,1'-biphenyl-2,2'-bisolato] cyclophosphacene (7) as products, as shown in Scheme 1.
Notas
Tesis (Licenciado en Química)
Proyecto FONDECYT 1130416.
Proyecto FONDECYT 1130416.
Palabras clave
Compuestos Orgánicos