Electron-Donating or -Withdrawing Nature of Substituents Revealed by the Electrochemistry of Metal-Free Phthalocyanines

The effect of substituents on the electrochemistry of metal-free phthalocyanines was examined for 17 phthalocyanine compounds. This work also provides new information about the electron-donating or -withdrawing nature of various substituents, namely, alkoxy, alkylthio, alkyl, alkynyl, phenyloxy, and...

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Bibliographic Details
Published in:Inorganic chemistry 2006-03, Vol.45 (5), p.2327-2334
Main Authors: Li, Renjie, Zhang, Xianxi, Zhu, Peihua, Ng, Dennis K. P, Kobayashi, Nagao, Jiang, Jianzhuang
Format: Article
Language:English
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Summary:The effect of substituents on the electrochemistry of metal-free phthalocyanines was examined for 17 phthalocyanine compounds. This work also provides new information about the electron-donating or -withdrawing nature of various substituents, namely, alkoxy, alkylthio, alkyl, alkynyl, phenyloxy, and phenylthio groups attached to the phthalocyanine system, from the viewpoint of electrochemistry. Most of the effects of peripheral and nonperipheral substitution and changes in the ring (π-conjugated system) size on the electrochemistry of metal-free phthalocyanines can be reasonably explained by considering the energy levels of frontier molecular orbitals of the corresponding compounds, which were obtained by calculations using the semiempirical PM3 method.
ISSN:0020-1669
1520-510X
DOI:10.1021/ic051931k