Flavin Analogue-Metal Ion Complexes Acting as Efficient Photocatalysts in the Oxidation of p-Methylbenzyl Alcohol by Oxygen under Irradiation with Visible Light

Shunichi Fukuzumi, Sadaki Kuroda, Toshio Tanaka

Research output: Contribution to journalArticlepeer-review

195 Scopus citations

Abstract

Flavin analogues (3-methyl-10-phenylisoalloxazine and 3-methyl-10-phenyl-5-deazaisoalloxazines) have been found to catalyze the photooxidation of p-methylbenzyl alcohol by oxygen efficiently in the presence of Mg2+ or Zn2+ ion in acetonitrile to yield p-methylbenzaldehyde and hydrogen peroxide under irradiation of the visible light of X > 360 nm. The Mg2+ or Zn2+ion forms a 1:1 complex with flavin analogues in acetonitrile. Such a complex formation between flavin analogues and the metal ion not only increases the oxidizing ability of the excited states of flavin analogues as indicated by the significant acceleration in the fluorescence quenching rate of flavin analogues with electron donors (methyl- and methoxy-substituted benzenes) by the complex formation but also stabilizes flavin analogues against irradiation with visible light to prevent the photodegradation of flavin analogues. The photocatalytic oxidation of p-methylbenzyl alcohol by oxygen is shown to proceed mainly via the singlet-excited states of flavin analogue-metal ion complexes acting as efficient photocatalysts.

Original languageEnglish
Pages (from-to)3020-3027
Number of pages8
JournalJournal of the American Chemical Society
Volume107
Issue number11
DOIs
StatePublished - May 1985

Fingerprint

Dive into the research topics of 'Flavin Analogue-Metal Ion Complexes Acting as Efficient Photocatalysts in the Oxidation of p-Methylbenzyl Alcohol by Oxygen under Irradiation with Visible Light'. Together they form a unique fingerprint.

Cite this