Design Of New Electropolymerized Polypyrrole Films Of Polyfluorinated Zn(ii) And Mn(iii) Porphyrins: Towards Electrochemical Sensors

New Zn (II) and Mn (III) porphyrins functionalized by one and four electropolymerizable pyrrole groups respectively have been synthesized and their electrochemical behavior was characterized in acetonitrile electrolyte. The electrooxidation of these metallopolyfluoroporphyrins has allowed the formation of N-substituted polypyrrole films. The latter exhibit electrochemical behaviors identical to those of the corresponding monomers combined with the conventional electroactivity of the polypyrrole skeleton. Moreover, the potential electrocatalytic properties of Mn (III)-based polypyrrole films in the presence of molecular oxygen and benzoic anhydride have been illustrated by cyclic voltammetry in organic solution. In addition, preliminary experiments have also demonstrated the potentialities of such polymeric films for the electrochemical detection of H2O2 in aqueous media. © 2007 Elsevier B.V. All rights reserved.285-6731738Cosnier, S., (2003) Anal. Bioanal. Chem., 377, p. 507(2000) The Porphyrin Handbook, Applications: Past, Present and Future, 6. , Kadish K.M., Smith K.M., and Guilard R. (Eds), Academic Press, LondonBiegsaga, M., Pyrzynska, K., Trojanowicz, M., (2000) Talanta, 51, p. 209Bedioui, F., Devynck, J., (1995) Acc. Chem. Res., 28, p. 30Carvalho de Medeiros, M.A., Cosnier, S., Deronzier, A., Moutet, J.-C., (1996) Inorg. Chem., 35, p. 2659Vilchez-Aguado, F., Gutierrez-Granados, S., Sucar-Succar, S., Bied-Charreton, C., Bedioui, F., (1997) New J. Chem., 21, p. 1009Cosnier, S., Walter, A., Montforts, F.-P., (1998) J. Porphyr. Phthalocyanines, 2, p. 39Bruti, E., Giannetto, M., Mori, G., Seeber, R., (1999) Electroanalysis, 11, p. 565Cosnier, S., Gondran, C., Wessel, R., Monforts, F.P., Wedel, M., (2000) J. Electroanal. Chem., 488, p. 83Wedel, M., Walter, A., Monforts, F.P., (2001) Eur. J. Org. Chem., p. 1681Griveau, S., Bedioui, F., (2001) Electroanalysis, 1, p. 13Diab, N., Schuhmann, W., (2001) Electrochim. Acta, 47, p. 265Cosnier, S., Gondran, C., Gorgy, K., Wessel, R., Montforts, F.-P., Wedel, M., (2002) Electrochem. Com., 4, p. 426Goux, A., Bedioui, F., Robbiola, L., Pontié, M., (2003) Electroanalysis, 15, p. 969Armijo, F., Goya, M., Gimeno, Y., Arévalo, M., Aguirre, M., Creus, A., (2006) Electrochem. Commun., 8, p. 779Battioni, P., Renaud, J.P., Bartoli, J.F., Reina-Artiles, M., Mansuy, D., (1988) J. Am. Chem. Soc., 110, p. 8462Ellis Jr., P.E., Lyons, J.E., (1989) J. Chem. Soc. Chem. Commun., p. 1189Ojima, F., Kobayashi, N., Osa, T., (1990) Bull. Chem. Soc. Jpn., 63, p. 1374Takeuchi, T., Gray, H.B., Goddard, W.A., (1994) J. Am. Chem. Soc., 116, p. 9730Carpio, H., Galeazzi, E., Greenhouse, R., Guzman, A., Velarde, E., Antonio, Y., Franco, F., Wren, D., (1982) Can. J. Chem., 60, p. 2295Kadish, K.M., Aroullo-MaAdams, C., Han, B.C., Franzen, M.M., (1990) J. Am. Chem. Soc., 112, p. 8364Kadish, K.M., (1986) Phys. Bioinorg. Chem. Ser., 34, p. 435Bidan, G., (1992) Sens. Actuators B, 6, p. 45Cauquis, G., Cosnier, S., Deronzier, A., Galland, B., Limosin, D., Moutet, J.C., Bizot, J., Pulicani, J.P., (1993) J. Electroanal. Chem., 352, p. 181Creager, S.E., Murray, R.W., (1987) Inorg. Chem., 26, p. 2612Cosnier, S., Deronzier, A., Roland, J.-F., (1990) J. Electroanal. Chem., 285, p. 133Deronzier, A., Devaux, R., Limosin, D., Latour, J.-M., (1992) J. Electroanal. Chem., 324, p. 325Albin, V., Bedioui, F., (2003) Electrochem. Com., 5, p. 129Nam, W., Kim, I., Lim, M.H., Choi, H.J., Lee, J.S., Jang, H.G., (2002) Chem. Eur. J., 8, p. 206