TY - JOUR
T1 - Formation and Isolation of a Four-Electron-Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin
AU - Suzuki, Wataru
AU - Kotani, Hiroaki
AU - Ishizuka, Tomoya
AU - Shiota, Yoshihito
AU - Yoshizawa, Kazunari
AU - Kojima, Takahiko
N1 - Funding Information:
This work was supported by Grants-in-Aid (24245011 and 17H03027) from the Japan Society of Promotion of Science (JSPS, MEXT) of Japan and a grant from the Yazaki Memorial Foundation for Science and Technology. We also appreciate Dr. Tatsuhiro Kojima (Osaka University) for helpful guidance in X-ray crystallography.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/2/12
Y1 - 2018/2/12
N2 - The two-electron reduction of a diprotonated dodecaphenylporphyrin derivative by Na2S2O4 gave a corresponding isophlorin (Iph) selectively. Formation of Iph was confirmed by spectroscopic measurements and the isolation of tetramethylated Iph. Further reduction of Iph proceeded to form an unprecedented four-electron-reduced porphyrin (IphH2), which was fully characterized by spectroscopic and X-ray crystallographic analysis. IphH2, with a unique conformation, could be oxidized to reproduce the starting porphyrin, resulting in a proton-coupled four-electron reversible redox system.
AB - The two-electron reduction of a diprotonated dodecaphenylporphyrin derivative by Na2S2O4 gave a corresponding isophlorin (Iph) selectively. Formation of Iph was confirmed by spectroscopic measurements and the isolation of tetramethylated Iph. Further reduction of Iph proceeded to form an unprecedented four-electron-reduced porphyrin (IphH2), which was fully characterized by spectroscopic and X-ray crystallographic analysis. IphH2, with a unique conformation, could be oxidized to reproduce the starting porphyrin, resulting in a proton-coupled four-electron reversible redox system.
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U2 - 10.1002/anie.201711058
DO - 10.1002/anie.201711058
M3 - Article
C2 - 29206356
AN - SCOPUS:85040649528
SN - 1433-7851
VL - 57
SP - 1973
EP - 1977
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 7
ER -