Amperometric determination of optically active 1-phenylethanol using chiral nitroxyl radical-modified polypyrrole films prepared by electrochemical polymerization

Yoshitomo Kashiwagi, Shinya Chiba, Jun Ichi Anzai

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Polymeric chiral nitroxyl radical catalysts were prepared on an electrode surface by electrochemical polymerization of (6S, 7R, 10R)-2,2,7-trimethyl-10- isopropyl-1-azaspiro[5.5]undecane-1-yloxyl precursors containing a pyrrole side chain. This modified electrode gave a reversible electron transfer for the nitroxyl radical/oxoammonium ion redox couple in cyclic voltammetry at +0.72 V vs. Ag|AgCl. The modified electrode was used for electrocatalytic oxidation of (R)-(+)- and (S)-(-)-1-phenylethanol as an optically active sec-alcohol. Cyclic voltammetric studies showed that the catalytic current for the oxidation of (S)-(-)-1-phenylethanol is greatly enhanced as compared with a small enhancement in the oxidation current for the (R)-isomer. The (S)-isomer can be detected selectively in a mixture of (R)-(+)- and (S)-(-)-1-phenylethanol, even in the presence of an excess amount of (R)-isomer.

Original languageEnglish
Pages (from-to)257-262
Number of pages6
JournalJournal of Electroanalytical Chemistry
Volume566
Issue number2
DOIs
Publication statusPublished - 2004 May 15

Keywords

  • Amperometric determination
  • Chiral nitroxyl radical
  • Cyclic voltammetry
  • Electrocatalytic oxidation
  • Electrochemical polymerization

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemical Engineering(all)
  • Electrochemistry

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