Synthesis of rigidified flavin-guanidinium ion conjugates and investigation of their photocatalytic properties

Schmaderer, Harald and Bhuyan, Mouchumi and Koenig, Burkhard (2009) Synthesis of rigidified flavin-guanidinium ion conjugates and investigation of their photocatalytic properties. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 5: 26. ISSN 1860-5397,

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Abstract

Flavin chromophores can mediate redox reactions upon irradiation by blue light. In an attempt to increase their catalytic efficacy, flavin derivatives bearing a guanidinium ion as oxoanion binding site were prepared. Chromophore and substrate binding site are linked by a rigid Kemp's acid structure. The molecular structure of the new flavins was confirmed by an X-ray structure analysis and their photocatalytic activity was investigated in benzyl ester cleavage, nitroarene reduction and a Diels-Alder reaction. The modified flavins photocatalyze the reactions, but the introduced substrate binding site does not enhance their performance.

Item Type: Article
Uncontrolled Keywords: ENANTIOSELECTIVE PHOTOCHEMICAL-REACTIONS; PHOTOINDUCED ELECTRON-TRANSFER; CONVERGENT FUNCTIONAL-GROUPS; DIELS-ALDER REACTION; HYDROGEN-PEROXIDE; MOLECULAR RECOGNITION; CATALYTIC-SYSTEM; REDOX PROPERTIES; OXIDATION; AMINES; flavin; guanidine; Kemp's acid; photocatalysis; template
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 15 Sep 2020 10:52
Last Modified: 15 Sep 2020 10:52
URI: https://pred.uni-regensburg.de/id/eprint/28957

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