CaracterizaciĆ³n electroquĆmica de 1-(2'-hidroxifenil)-3-fenil-2-propen-1-onas y 1-(2'-hidroxifenil)-3-ferrocenil-2-propen-1-onas sustituidas
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Fecha
2016
Autores
Profesor/a GuĆa
Facultad/escuela
Idioma
es
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Universidad AndrƩs Bello
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Licencia CC
Licencia CC
Resumen
En esta Unidad de InvestigaciĆ³n, reportamos la caracterizaciĆ³n electroquĆmica y Uv-Vis de nuevas ferrocenil-chalconas y bichalconas. Dado que estos compuestos no han sido previamente descritos en la literatura, decidimos iniciar su estudio aislando las seƱales electroquĆmicas derivadas de cada uno de los grupos funcionales presentes en este tipo de molĆ©culas. Se considerĆ³ que la ferrocenil chalcona estĆ” formada por tres fragmentos consecutivos, correspondientes a cada uno de los grupos funcionales presentes en la molĆ©cula: un ferroceno, un enlace doble y una porciĆ³n 2Ā“-acetofenona, todas ellas unidas entre sĆ para formar la ferrocenil chalcona. Primero estudiamos las seƱales electroquĆmicas derivadas del ferroceno, luego, agregamos un enlace doble a la estructura, asĆ el vinil-ferroceno sirviĆ³ como compuesto modelo. Para aislar las seƱales electroquĆmicas correspondientes a la porciĆ³n de la 2Ā“- hidroxiacetofenona, se usĆ³ la chalcona orgĆ”nica comercial 2Ā“- hidroxichalcona. De esta manera las seƱales caracterĆsticas del ferroceno, del doble enlace y de la acetofenona fueron caracterizadas, encontrĆ”ndose que aparecen seƱales de oxidaciĆ³n a 445, 1668, 1231 mV, respectivamente.
Dado que los dos brazos de las ferrocenil-bichalconas son idĆ©nticos entre sĆ, y estructuralmente idĆ©nticos a las ferrocenil-chalconas estudiadas, encontramos que ambas presentan el mismo perfil voltamperomĆ©trico. Adicionalmente, ya que en la literatura pueden ser encontrados algunos compuestos conteniendo ferroceno directamente unido a un doble enlace, que han sido descritos como sensores selectivos de Cu2+, decidimos probar si el vinil-ferroceno podĆa funcionar del mismo modo. Se realizaron Voltamperogramas cĆclicos mediante los cuales se evidenciĆ³ la formaciĆ³n de un complejo vinil-ferrocenoāCu. (1050 mV) el que fue corroborado mediante espectroscopia Uv-Vis (ļ¬max= 750 nm). Finalmente, tras la adiciĆ³n de Ni2+ y Zn2+ a una soluciĆ³n de vinil-ferroceno no se observaron cambios en su perfil voltamperomĆ©trico, dando cuenta de su selectividad frente a Cu2+.
In this work we report on both the electrochemical and UV-Vis spectroscopic characterization of new ferrocenyl-chalcones and bichalcones. Since these compounds are not previously electrochemically studied, we decided to initiate their study by isolating the electrochemical signals derived from each functional group present in these kind of molecules. To do that, the ferrocenyl chalcone was considered to be formed by three consecutive functional group fragments: a ferrocene, a double bond, and a 2Ā“-hydroxyacetophenone moiety, all of them linked together to form a ferrocenyl-chalcone. We first studied the electrochemical signals derived from ferrocene, then we added the double bond to the structure, i.e. the vinyl-ferrocene served as a model compound in that case. To isolate the electrochemical signals of the 2Ā“-hydroxyacetophenone portion, the commercial organic 2Ā“-hydroxychalcone was finally used. In this way the characteristic electrochemical signals for the ferrocene, double bond, and acetophenone moieties present in the ferrocenylāchalcones were characterized and found to appear at: 445, 1668, 1231 mV, respectively. Since the arms of the ferrocenyl bichlacones are identical between them and structurally identical to the ferrocenyl-chalcones studied, we found that ferrocenyl-bichalcones presented the same characteristic electrochemical signals found for ferrocenyl-chalcones. Additionally, since some compounds bearing a ferrocene linked to a double bond has been described as selective sensors for Cu2+, we decided to test if the vinyl-ferrocene moiety of the ferrocenyl-chlacones behaves as well as a sensor for Cu2+ ions. To do that, electrochemical experiments were conducted to evidence the formation of the vinyl-ferroceneāCu complex, and its selectivity against Cu, Zn and Ni. The characteristic electrochemical signals for the complex were found to appear at 1050 mV, and selectivity against Cu2+ions was showed. The existence of the complex was also detected via Uv-Vis spectroscopy, being their characteristic ļ¬max found to be 750 nm.
In this work we report on both the electrochemical and UV-Vis spectroscopic characterization of new ferrocenyl-chalcones and bichalcones. Since these compounds are not previously electrochemically studied, we decided to initiate their study by isolating the electrochemical signals derived from each functional group present in these kind of molecules. To do that, the ferrocenyl chalcone was considered to be formed by three consecutive functional group fragments: a ferrocene, a double bond, and a 2Ā“-hydroxyacetophenone moiety, all of them linked together to form a ferrocenyl-chalcone. We first studied the electrochemical signals derived from ferrocene, then we added the double bond to the structure, i.e. the vinyl-ferrocene served as a model compound in that case. To isolate the electrochemical signals of the 2Ā“-hydroxyacetophenone portion, the commercial organic 2Ā“-hydroxychalcone was finally used. In this way the characteristic electrochemical signals for the ferrocene, double bond, and acetophenone moieties present in the ferrocenylāchalcones were characterized and found to appear at: 445, 1668, 1231 mV, respectively. Since the arms of the ferrocenyl bichlacones are identical between them and structurally identical to the ferrocenyl-chalcones studied, we found that ferrocenyl-bichalcones presented the same characteristic electrochemical signals found for ferrocenyl-chalcones. Additionally, since some compounds bearing a ferrocene linked to a double bond has been described as selective sensors for Cu2+, we decided to test if the vinyl-ferrocene moiety of the ferrocenyl-chlacones behaves as well as a sensor for Cu2+ ions. To do that, electrochemical experiments were conducted to evidence the formation of the vinyl-ferroceneāCu complex, and its selectivity against Cu, Zn and Ni. The characteristic electrochemical signals for the complex were found to appear at 1050 mV, and selectivity against Cu2+ions was showed. The existence of the complex was also detected via Uv-Vis spectroscopy, being their characteristic ļ¬max found to be 750 nm.
Notas
Tesis (Licenciado en QuĆmica)
Proyecto FONDECYT 11130505
Proyecto FONDECYT 11130505
Palabras clave
ElectroquĆmica, Chalconas