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Oxygen Reduction Catalyzed by a Fluorinated Tetraphenylporphyrin Free Base at Liquid/Liquid Interfaces
(Amer Chemical Soc, 2010) Hatay, İmren; Su, Bin; Mendez, Manuel A.; Corminboeuf, Clemence; Khoury, Tony; Gros, Claude P.; Bourdillon, Melanie; Meyer, Michel; Barbe, Jean-Michel; Ersöz, Mustafa; Zális, Stanislav; Samec, Zdenek; Girault, Hubert H.
The diprotonated form of a fluorinated free base porphyrin, namely 5-(p-aminophenyl)-10,15,20-tris(pentafluorophenyl)porphyrin (H(2)FAP), can catalyze the reduction of oxygen by a weak electron donor, namely ferrocene (Fc). At a water/1,2-dichloroethane interface, the interfacial formation of H(4)FAP(2+) is observed by UV-vis spectroscopy and ion-transfer voltammetry, due to the double protonation of H(2)FAP at the imino nitrogen atoms in the tetrapyrrole ring. H(4)FAP(2+) is shown to bind oxygen, and the complex in the organic phase can easily be reduced by Fc to produce hydrogen peroxide as studied by two-phase reactions with the Galvani potential difference between the two phases being controlled by the partition of a common ion. Spectrophotometric measurements performed in 1,2-dichloroethane solutions clearly evidence that reduction of oxygen by Fc catalyzed by H(4)FAP(2+) only occurs in the presence of the tetrakis(pentafluorophenyl)borate (TB(-)) counteranion in the organic phase. Finally, ab initio computations support the catalytic activation of H(4)FAP(2+) on oxygen.