{7-[Bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl Derivatives for Photorelease of Carboxylic Acids, Alcohols/Phenols, Thioalcohols/Thiophenols, and Amines

Light‐induced release of biomolecules from inactive precursor molecules represents a powerful method to study cellular processes with high temporal and spatial resolution. Here we report the synthesis and photochemistry of a series of {7‐[bis(carboxymethyl)amino]coumarin‐4‐yl}methyl carboxylates, carbonates, carbamates, and thiocarbonates as potential phototriggers for compounds with COOH, OH, NH2, and SH functions. The compounds are soluble in aqueous buffer, show low fluorescence, and are efficiently photolysed by irradiation with UV/Vis or IR light to release carboxylates, alcohols, phenols, amines, thioalcohols, or thiophenols. Light‐induced deprotection: A series of novel phototriggers based on the coumarinylmethyl chromophore were prepared. The compounds are soluble in aqueous buffer and are efficiently photolysed under non‐damaging light conditions upon one‐ and two‐photon flash photolysis (see graphic).