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The catalytic two-electron reduction of dioxygen (O 2 ) by octamethylferrocene (Me 8 Fc) occurs with a metal-free triphyrin (HTrip) in the presence of perchloric acid (HClO 4 ) in benzonitrile (PhCN) at 298 K to yield Me 8 Fc + and H 2 O 2 . Detailed kinetic analysis has revealed that the catalytic two-electron reduction of O 2 by Me 8 Fc with HTrip proceeds via proton-coupled electron transfer from Me 8 Fc to HTrip to produce H 3 Trip˙ + , followed by a second electron transfer from Me 8 Fc to H 3 Trip˙ + to produce H 3 Trip, which is oxidized by O 2  via formation of the H 3 Trip/O 2 complex to yield H 2 O 2 . The rate-determining step in the catalytic cycle is hydrogen atom transfer from H 3 Trip to O 2 in the H 3 Trip/O 2 complex to produce the radical pair (H 3 Trip˙ + HO 2 ˙) as an intermediate, which was detected as a triplet EPR signal with fine-structure by the EPR measurements at low temperature. The distance between the two unpaired electrons in the radical pair was determined to be 4.9 Å from the zero-field splitting constant ( D ).

Catalytic two-electron reduction of dioxygen catalysed by metal-free [14]triphyrin(2.1.1)