TY - JOUR
T1 - Reversible transformation between the oxidized and reduced forms of redox coenzyme analogues
AU - Fukuzumi, Shunichi
AU - Tanii, Kumiko
AU - Ishikawa, Masashi
AU - Tanaka, Toshio
PY - 1989
Y1 - 1989
N2 - Reversible transformation between 10-methylacridinium ion (AcrH +) and 9,10-dihydro-10-methylacridine (AcrH2) has been achieved by combining the photo-reduction of AcrH+ by benzyl alcohol derivatives in MeCN at 298 K under irradiation of visible light of λ > 360 nm with the thermal oxidation of AcrH2 by the corresponding benzaldehyde derivatives at 333 K. The photo-reduction of AcrH+ by a benzyl alcohol derivative can also be combined with the photo-oxidation of AcrH2 by dibenzyl disulphide under irradiation of light of λ 285 nm which corresponds to the absorption maximum of AcrH2. Under continuous irradiation of light from a Xenon lamp, the AcrH+/ AcrH2 redox pair acts as a photocatalyst for the oxidation of p-chlorobenzyl alcohol by dibenzyl disulphide to yield p-chlorobenzaldehyde and toluene-α-thiol. Reversible transformation between riboflavin-2′, 3′,4′,5′-tetra-acetate (Fl) and the corresponding 1,5-dihydroflavin (FlH2) has also been achieved by utilizing all possible combinations of thermal and photochemical reactions in controlling the direction of the redox reaction between Fl and benzenethiol derivatives, i.e., the forward thermal reduction of Fl by benzenethiol derivatives combined with the reverse photo-oxidation of FlH2 by the corresponding disulphides, the forward photo-reduction of Fl and the reverse photo-oxidation of FlH 2 under irradiation with light of different wavelengths, and the forward photo-reduction of Fl combined with the reverse thermal oxidation of FlH2.
AB - Reversible transformation between 10-methylacridinium ion (AcrH +) and 9,10-dihydro-10-methylacridine (AcrH2) has been achieved by combining the photo-reduction of AcrH+ by benzyl alcohol derivatives in MeCN at 298 K under irradiation of visible light of λ > 360 nm with the thermal oxidation of AcrH2 by the corresponding benzaldehyde derivatives at 333 K. The photo-reduction of AcrH+ by a benzyl alcohol derivative can also be combined with the photo-oxidation of AcrH2 by dibenzyl disulphide under irradiation of light of λ 285 nm which corresponds to the absorption maximum of AcrH2. Under continuous irradiation of light from a Xenon lamp, the AcrH+/ AcrH2 redox pair acts as a photocatalyst for the oxidation of p-chlorobenzyl alcohol by dibenzyl disulphide to yield p-chlorobenzaldehyde and toluene-α-thiol. Reversible transformation between riboflavin-2′, 3′,4′,5′-tetra-acetate (Fl) and the corresponding 1,5-dihydroflavin (FlH2) has also been achieved by utilizing all possible combinations of thermal and photochemical reactions in controlling the direction of the redox reaction between Fl and benzenethiol derivatives, i.e., the forward thermal reduction of Fl by benzenethiol derivatives combined with the reverse photo-oxidation of FlH2 by the corresponding disulphides, the forward photo-reduction of Fl and the reverse photo-oxidation of FlH 2 under irradiation with light of different wavelengths, and the forward photo-reduction of Fl combined with the reverse thermal oxidation of FlH2.
UR - http://www.scopus.com/inward/record.url?scp=37049082144&partnerID=8YFLogxK
U2 - 10.1039/p29890001801
DO - 10.1039/p29890001801
M3 - Article
AN - SCOPUS:37049082144
SN - 1472-779X
SP - 1801
EP - 1806
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
IS - 11
ER -