Daniel T. Gryko
Polish Academy of Sciences, Poland
Title: Diketopyrrolopyrroles - the journey from ferrari pigments to fluorescent functional dyes
Biography
Biography: Daniel T. Gryko
Abstract
Two-photon absorption (2PA) is a non-linear optical phenomenon with broad scope of applications. It has already been applied, or is under intensive investigation, in fields such as: optical limiting, polymerization-microfabrication, 3D-data storage, photodynamic therapy, two-photon excited fluorescence etc.1Structurally unique π-expanded diketopyrrolopyrroles were designed and synthesized. Strategic placement of a fluorene scaffold at the periphery of a diketopyrrolopyrrole via tandem Friedel-Crafts-dehydratation reactions,2 resulted in dyes with supreme solubility. Despite the extended ring system, the dye still preserved good solubility and was further functionalized using Pd-catalyzed coupling reactions, such as Buchwald-Hartwig amination. By placing two amine groups at peripheral positions of the resulting dyes, we have achieved values of two-photon absorption cross-section on the level of 2000 GM around 1000 nm, which generated a two-photon brightness of ~1600 GM. These characteristics in combination with red emission (665 nm) make these new π-expanded diketopyrrolopyrroles of major promise as two-photon dyes for bioimaging applications.
