A remarkably stable acyclic phosphamethine cyanine dye

Abstract

While cyanine dyes enjoy a multitude of uses in science and technology, their phosphorus analogues, phosphamethine cyanine dyes, have not yet found benchtop applications primarily because of their sensitivity to air and moisture. We are excited to report full characterization of an extraordinarily stable acyclic phosphamethine cyanine dye. Nitrile substituents on the N-heterocyclic framework afford air and water stability as well as resistance to methylation and sulfuration even under forcing conditions. Cyclic voltammetry confirms a high oxidation potential of the compound and computational investigations reveal stabilized orbitals. The unusual orbital stability appears to render the normally electron-rich P^I site an extremely poor nucleophile and difficult to oxidize. From a practical perspective, this dye is prepared in a one-pot method under mild conditions.