Electron-donating or -withdrawing nature of substituents revealed by the electrochemistry of metal-free phthalocyanines

Renjie Li, Xianxi Zhang, Peihua Zhu, Dennis K.P. Ng, Nagao Kobayashi, Jianzhuang Jiang

Research output: Contribution to journalArticlepeer-review

141 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2327-2334
Number of pages8
JournalInorganic chemistry
Volume45
Issue number5
DOIs
Publication statusPublished - 2006 Mar 6

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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