Palladium-catalyzed Suzuki reactions of brominated flavin derivatives (5-deazaflavins, alloxazines, and isoalloxazines) with boronic acids or boronic acid esters that occur readily under mild conditions were shown to be an effective tool for the synthesis of a broad range of 7/8-arylflavins. In general, the introduction of an aryl/heteroaryl group by means of a direct C-C bond has been shown to be a promising approach to tuning the photophysical properties of flavin derivatives. The aryl substituents caused a bathochromic shift in the absorption spectra of up to 52 nm and prolonged the fluorescence lifetime by up to 1 order of magnitude. Moreover, arylation of flavin derivatives decreased their ability to generate singlet oxygen.

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 166 28Prague 6 Czech Republic

Faculty of Chemistry Adam Mickiewicz University Uniwersytetu Poznańskiego 8 61 614Poznań Poland

Citace poskytuje Crossref.org

Fast singlet excited-state deactivation pathway of flavin with a trimethoxyphenyl derivative