Preparation, electrochemical and spectral properties of N-methylated pyridylethynyl porphyrins

Dalton Transactions : an International Journal of Inorganic Chemistry
Ching-Yao LinWen-Jwu Wang

Abstract

A new series of electron-deficient porphyrins were prepared by attaching one or two N-methylated 2-, 3- or 4-pyridylethynyl groups to the 10,20-meso positions of (5,15-biphenylporphinato)zinc(II). Electrochemical studies showed significant changes in the reduction potentials of these porphyrins, and N-methyl-2-pyridylethyne is the strongest electron-withdrawing substituent in the series. UV-visible spectra demonstrated largely red-shifted absorptions, and N-methyl-4-pyridylethyne has the greatest impact to the porphyrin absorptions. Electrochemical, UV-visible and EPR results concluded that porphyrins Zn2 and Zn6 reversibly undergo two one-electron porphyrin-ring reductions to their anion radicals then dianions. The first reductions of porphyrins Zn1, Zn3, Zn4 and Zn5 were irreversible one-electron transfer processes. The instability of these reduction products was suggested to result from the eletrophilic attacks at the substituents.

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Citations

Mar 22, 2006·Chemical Communications : Chem Comm·Chen-Fu LoChing-Yao Lin
Nov 21, 2014·Chemical Communications : Chem Comm·Sung-Chou Huang, Ching-Yao Lin
Feb 2, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Ching-Yao LinYi-Hui Cheng

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