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Reorganization Energies of Diprotonated and Saddle-Distorted Porphyrins in Photoinduced Electron-Transfer Reduction Controlled by Conformational Distortion

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Department of Material and Life Science, Graduate School of Engineering, Osaka University and SORST (JST), 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan
[email protected]; [email protected]
Cite this: J. Am. Chem. Soc. 2009, 131, 2, 577–584
Publication Date (Web):December 19, 2008
https://doi.org/10.1021/ja806261q
Copyright © 2008 American Chemical Society
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Abstract

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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 ([H4DPP]Cl2), tetrakis(2,4,6-trimethylphyenyl)porphyrin ([H4TMP]Cl2), tetraphenylporphyrin ([H4TPP]Cl2), and octaphenylporphyrin ([H4OPP]Cl2), were investigated in comparison with those of a planar porphyrin, zinc [tetrakis(pentafluorophenyl)]porphyrin [Zn(F20TPP)(CH3CN)], in deaerated acetonitrile by laser flash photolysis. The resulting 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 [H4TMP]Cl2, 1.29 eV for [H4TPP]Cl2, 1.45 eV for [H4OPP]Cl2, 1.69 eV for [H4DPP]Cl2, and 0.84 eV for [Zn(F20TPP)(CH3CN)]. 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 by conformational distortions of the porphyrin ring. This indicates that the reorganization energy of electron transfer is governed by structural change, giving a larger contribution of inner-sphere bond reorganization energy rather than outer-sphere solvent reorganization energy.

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CV and DPV traces, plots of fluorescence decay, phosphorescence spectra for [H4TPP]Cl2, [H4OPP]Cl2, and [H4DPP]Cl2; transient absorption spectra, CV, and phosphorescence spectrum of [H4TMP]Cl2 and [Zn(F20TPP)(MeCN)]; full author list of ref 37. This material is available free of charge via the Internet at http://pubs.acs.org.

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