Electrogenerated chemiluminescence of sterically hindered porphyrins in aqueous media

Fang-Chung Chen, J. H. Ho, C. Y. Chen, Y. O. Su*, T. I. Ho

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

A sterically hindered water-soluble porphyrin, tetrakis(3-sulfonatomesityl)porphyrin (H2TSMP), could form stable radical cation in aqueous media after electrochemical one electron oxidation. The anodic oxidation of H2TSMP in the presence of tripropylamine or C2O42- as a coreactant in aqueous solution produces electrogenerated chemiluminescence (ECL) with maxima at 640 and 700 nm. The same emission spectrum of ECL and fluorescence indicates that the ECL emission is from the singlet state of H2TSMP. The annihilation reactions of ZnTSMP·+ and ZnTSMP·-, which are generated electrochemically, in CH3CN + H2O (1:1) mixed solution results in an emission which is identical to the photoluminescence. Protection of the active sites against the nucleophilic attack of water or OH- by sterical hinderance is a successful strategy in designing new ECL-active compounds in aqueous media. Both ECL reaction mechanisms are proposed.

Original languageEnglish
Pages (from-to)17-23
Number of pages7
JournalJournal of Electroanalytical Chemistry
Volume499
Issue number1
DOIs
StatePublished - 23 Feb 2001

Keywords

  • Electrogenerated chemiluminescence
  • Porphyrins
  • Sterically hindered

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