The chemistry of 6-hydroxyflavylium: Zwitterionic base and p-quinoidal chalcones. A multiswitchable system operated by proton, electron and photon inputs

Abstract

The complex network of chemical reactions of the compound 6-hydroxyflavylium perchlorate was studied by different techniques including UV-vis absorption spectrophotometry, stopped-flow, electrochemistry, and photochemistry. The network is characterized by the formation of a very reactive zwitterionic base as well as by p-quinoidal chalcones. The trans-chalcone is metastable in very acidic solutions and exhibits reversible redox reactions, allowing to introduce for the first time in the flavylium network an electrochemical input. © 2007 The Royal Society of Chemistry and Owner Societies.