Polar Diketopyrrolopyrrole-Imidazolium Salts as Selective Probes for Staining Mitochondria in Two-Photon Fluorescence Microscopy

Three rationally designed polar derivatives of diketopyrrolopyrrole consisting of 1,3-dimethylimidazolium cationic units and benzene, thiophene, or furan rings as spacers were synthesized and thoroughly studied. The obtained salts are soluble in polar organic solvents and show satisfactory solubility in water, which makes them suitable for the applications in bioimaging. Photophysical measurements revealed that the obtained derivatives are characterized by strong absorption and good fluorescence quantum yields. The corresponding two-photon properties were also examined and showed that the synthesized salts exhibit large two-photon absorption cross-sections reaching 4000GM (GM=Goeppert-Mayer unit, 1GM=10(-50)cm(4)sphoton(-1)) and very high two-photon brightness values exceeding 2000GM. It was demonstrated that these salts can be safely applied in two-photon fluorescence microscopy for selective staining of mitochondria in living cells.