Pyrylenes: A New Class of Tunable, Redox-Switchable, Photoexcitable Pyrylium

By Antoni, Patrick W.; Hansmann, Max M.
Published in Journal of the American Chemical Society 2018

Abstract

A new synthetic and modular access to a large family of redox-switchable molecules based upon the combination of pyrylium salts and carbenes is presented. The redox-properties of this new molecule class correlate very well with the ?-accepting properties of the corresponding carbenes. While the pyrylium moiety acts as a chromophore, the carbene moiety can tune the redox-properties and stabilize the corresponding radicals. This leads to the isolation of the first monomeric pyranyl-radical in the solid-state. The three stable oxidation states could be cleanly accessed by chemical oxidation, characterized by NMR, EPR, UV

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