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Kinetics of photoinduced electron transfer from a series of electron donors to the triplet excited states of a series of nonplanar porphyrins, hydrochloride salts of saddle-distorted dodecaphenylporphyrin ([H 4 DPP]Cl 2 ), tetrakis(2,4,6-trimethylphyenyl)porphyrin ([H 4 TMP]Cl 2 ), tetraphenylporphyrin ([H 4 TPP]Cl 2 ), and octaphenylporphyrin ([H 4 OPP]Cl 2), were investigated in comparison with those of a planar porphyrin, zinc [tetrakis(pentafluorophenyl)]porphyrin [Zn(F 20 TPP)(CH 3 CN)], in deaerated acetonitrile by laser flash photolysis. Theresulting data were evaluated in light of the Marcus theory of electron transfer, allowing us to determine reorganization energies of electron transfer to be 1.21 eV for [H 4 TMP]Cl 2 ,1.29 eV for [H 4 TPP]Cl 2 , 1.45 eV for [H 4 OPP]Cl 2 , 1.69 eV for [H 4 DPP]Cl 2 , and 0.84 eV for [Zn(F 20 TPP)(CH 3 CN)]. The reorganization energies exhibited a linear correlation relative to the out-of-plane displacements, which represent the degree of nonplanarity. The rate of electron-transfer reduction of diprotonated porphyrins is significantly slowed down byconformational distortions of the porphyrin ring. This indicates that t he reorganization energy of electron transfer is governed by structural change, giving a larger contribution of inner-sphere bond reorganizationenergy rather than outer-sphere solvent reorganization energy.
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Reference：
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion