Dadova, Jitka and Kuemmel, Susanne and Feldmeier, Christian and Cibulkova, Jana and Pazout, Richard and Maixner, Jaroslav and Gschwind, Ruth M. and Koenig, Burkhard and Cibulka, Radek (2013) Aggregation Effects in Visible-Light Flavin Photocatalysts: Synthesis, Structure, and Catalytic Activity of 10-Arylflavins. CHEMISTRY-A EUROPEAN JOURNAL, 19 (3). pp. 1066-1075. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
A series of 10-arylflavins (10-phenyl-, 10-(2',6'-dimethylphenyl)-, 10-(2',6'-diethylphenyl)-, 10-(2',6'-diisopropylphenyl)-, 10-(2'-tert-butylphenyl)-, and 10-(2',6'-dimethylphenyl)-3-methylisoalloxazine (2?af)) was prepared as potentially nonaggregating flavin photocatalysts. The investigation of their structures in the crystalline phase combined with 1H-DOSY NMR spectroscopic experiments in CD3CN, CD3CN/D2O (1:1), and D2O confirm the decreased ability of 10-arylflavins 2 to form aggregates relative to tetra-O-acetyl riboflavin (1). 10-Arylflavins 2?ad do not interact by pp interactions, which are restricted by the 10-phenyl ring oriented perpendicularly to the isoalloxazine skeleton. On the other hand, N3?H...O hydrogen bonds were detected in their crystal structures. In the structure of 10-aryl-3-methylflavin (2?f) with a substituted N3 position, weak C?H...O bonds and weak pp interactions were found. 10-Arylflavins 2 were tested as photoredox catalysts for the aerial oxidation of 4-methoxybenzyl alcohol to the corresponding aldehyde (model reaction), thus showing higher efficiency relative to 1. The quantum yields of 4-methoxybenzyl alcohol oxidation reactions mediated by arylflavins 2 were higher by almost one order of magnitude relative to values in the presence of 1.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOINDUCED ELECTRON-TRANSFER; BENZYL ALCOHOL DERIVATIVES; BAEYER-VILLIGER REACTION; SENSITIZED PHOTOOXIDATION; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; FLAVOENZYME ACTIVITY; AROMATIC STACKING; REDOX PROPERTIES; PI INTERACTIONS; aggregation; flavins; noncovalent interactions; organocatalysis; oxidation; photocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Apr 2020 09:28 |
| Last Modified: | 29 Apr 2020 09:28 |
| URI: | https://pred.uni-regensburg.de/id/eprint/17510 |
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