A Convenient Synthesis of Diketopyrrolopyrrole Dyes
Vítor A. S. Almodôvar, Augusto C. Tomé
Abstract
]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from Pigment Red 254, an inexpensive commercial pigment. The synthesis includes a Suzuki-Miyaura cross-coupling reaction of a bis(4-chlorophenyl)DPP derivative with aryl and hetaryl boronic acids under mild reaction conditions. The new dyes show large Stokes shifts and high fluorescence quantum yields, important features for their potential use in technical and biological applications.
Topics & Concepts
FluorescencePhotothermal therapyCombinatorial chemistrySuzuki reactionPigmentArylBoronic acidNanotechnologyDerivative (finance)ChemistryCoupling reactionMaterials sciencePhotochemistryOrganic chemistryCatalysisOpticsEconomicsPhysicsFinancial economicsAlkylPorphyrin and Phthalocyanine ChemistryElectrochemical sensors and biosensorsAdvanced Nanomaterials in Catalysis