Preparación de derivados de perilenodiimida para comparar su capacidad de adhesión a nanotubos de carbono con la de derivados de 3,6- difeniltetrazina
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2016-02-19
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Jaén: Universidad de Jaén
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[ES] Desde el momento en que se dispuso de nanomateriales grafénicos para su estudio
experimental (básicamente nanotubos de carbono y grafeno), no han cesado de
aportarse pruebas que confirman las extraordinarias propiedades físicas y físicoquímicas
de estos material, lo que está permitiendo diseñar aplicaciones de los
mismos en tecnologías avanzadas. Sin embargo, la realización de las
extraordinarias expectativas creadas alrededor de dichos materiales depende de que
seamos capaces de generar conocimiento y tecnologías que nos permitan controlar
su manejo y transformación. En este sentido, la funcionalización no-covalente a
través de enlaces π-π constituye una de las vías más prometedoras para conseguir
la introducción de funciones químicas en los nanomateriales de grafeno, porque
permite mantener su estructura libre de defectos y de reacciones laterales no
deseadas. Este tipo de funcionalización es dependiente de la existencia de sistemas
aromáticos capaces de establecer fuertes interacciones de tipo π-π con el sistema
conjugado extendido de las superficies grafénicas, de modo que sirvan de unidades
de anclaje, a través de las cuales poder sujetar las funciones químicas deseadas
sobre dichas superficies.
En este trabajo se han sintetizado tres bisiimidas derivadas de perileno con cadenas
laterales hidrofílicas buscando un derivado de este sistema aromático con suficiente
solubilidad en medio acuoso. Aunque dos de ellas tienen una solubilidad muy
limitada, finalmente hemos preparado, a través de una síntesis multietapa, un
derivado con cadenas laterales de poliamina ramificada y con todos los nitrógenos
formando parte de aminas terciarias (dos de ellos formando parte de restos de
morfolina) que conseguía dicha solubilidad. Este compuesto nos permitirá disponer
de una referencia para comparar la intensidad de las interacciones de tipo π-π de
otros sistemas aromáticos y heteroaromáticos de interés en la funcionalización de
superficies grafénicas.
[EN] Since graphene nanomaterials are available for experimental study, around two decades ago, evidences that confirm the extraordinary physical and physicochemical properties of this material have continuously been provided, thus enabling to design new same applications of these materials in advanced technologies. However, the realization of the great expectations created around the graphene nanomaterials depends on our ability to generate knowledge and technologies that allow controlling their management and transformation. In this sense, the noncovalent functionalization through π-π bond is one of the most promising avenues to achieve the introduction of chemical functions in graphene and CNT while keeping their structure free of defects and unwanted side reactions. This type of functionalization is dependent on the existence of aromatic systems capable of establishing strong interactions of the π-π type with the extended conjugated graphenes sheet, so they could be used as the anchoring units whereby holding the desired chemical functions onto the graphene-like surfaces. In this work we prepared three perylene bisimide derivatives bearing hydrophilic lateral chains with the aim of attaining a derivative of such aromatic nucleus possessing a high solubility in aqueous media. Two of our synthesized molecules showed a very limited solubility. However we finally prepared, through a multistep synthesis, a new perylene bisimide derivative carrying branched polyamines with all their nitrogen atoms in the form tertiary amines (two of them as part of morpholine rings) which possess the required solubility properties. This derivative allow us to have a sort of reference standard to which refer the intensity of the π-π interactions stablished between graphene-like surfaces and other aromatic and heteroaromatic systems of interest.
[EN] Since graphene nanomaterials are available for experimental study, around two decades ago, evidences that confirm the extraordinary physical and physicochemical properties of this material have continuously been provided, thus enabling to design new same applications of these materials in advanced technologies. However, the realization of the great expectations created around the graphene nanomaterials depends on our ability to generate knowledge and technologies that allow controlling their management and transformation. In this sense, the noncovalent functionalization through π-π bond is one of the most promising avenues to achieve the introduction of chemical functions in graphene and CNT while keeping their structure free of defects and unwanted side reactions. This type of functionalization is dependent on the existence of aromatic systems capable of establishing strong interactions of the π-π type with the extended conjugated graphenes sheet, so they could be used as the anchoring units whereby holding the desired chemical functions onto the graphene-like surfaces. In this work we prepared three perylene bisimide derivatives bearing hydrophilic lateral chains with the aim of attaining a derivative of such aromatic nucleus possessing a high solubility in aqueous media. Two of our synthesized molecules showed a very limited solubility. However we finally prepared, through a multistep synthesis, a new perylene bisimide derivative carrying branched polyamines with all their nitrogen atoms in the form tertiary amines (two of them as part of morpholine rings) which possess the required solubility properties. This derivative allow us to have a sort of reference standard to which refer the intensity of the π-π interactions stablished between graphene-like surfaces and other aromatic and heteroaromatic systems of interest.