title: Polar diketopyrrolopyrrole-imidazolium salts as selective probes for staining mitochondria in two-photon fluorescence microscopy.
abstract: Three rationally designed polar derivatives of diketopyrrolopyrrole consisting of 1,3-dimethylimidazolium cationic units and benzene, thiophene, or furan rings as π 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 4000 GM (GM=Goeppert-Mayer unit, 1 GM=10(-50)  cm(4)  s photon(-1) ) and very high two-photon brightness values exceeding 2000 GM. It was demonstrated that these salts can be safely applied in two-photon fluorescence microscopy for selective staining of mitochondria in living cells.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland).
authors.forename: Marek
authors.initials: M
authors.lastname: Grzybowski
authors.affiliation: Department of Laboratory Diagnostics and Clinical Immunology of Developmental Age, Medical University of Warsaw, Marszałkowska 24, 00-576 Warsaw (Poland).
authors.forename: Eliza
authors.initials: E
authors.lastname: Glodkowska-Mrowka
authors.affiliation: Institut des Sciences Moléculaires, Université Bordeaux 1 (CNRS UMR 5255), Bâtiment A12, 351 cours de la liberation 33405 TALENCE cedex (France).
authors.forename: Vincent
authors.initials: V
authors.lastname: Hugues
authors.affiliation: Laboratory of Imaging Tissue Structure and Function, Nencki Institute of Experimental Biology, Polish Academy of Sciences, Pasteura 3, 02-093 Warsaw (Poland).
authors.forename: Wojciech
authors.initials: W
authors.lastname: Brutkowski
authors.affiliation: Institut des Sciences Moléculaires, Université Bordeaux 1 (CNRS UMR 5255), Bâtiment A12, 351 cours de la liberation 33405 TALENCE cedex (France).
authors.forename: Mireille
authors.initials: M
authors.lastname: Blanchard-Desce
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland). dtgryko@icho.edu.pl.
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Gryko
mesh_terms: D002412:Cations / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells / Q000737:chemistry*; D006801:Humans; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008856:Microscopy, Fluorescence; D008928:Mitochondria / Q000737:chemistry*; D017785:Photons; D011758:Pyrroles / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D013194:Staining and Labeling; D014867:Water
chemical_list: C516814:1,3-dimethylimidazolium; D002412:Cations; D005456:Fluorescent Dyes; D007093:Imidazoles; D007659:Ketones; D011758:Pyrroles; D012492:Salts; D012997:Solvents; C000604894:diketopyrrolopyrrole dye; D014867:Water
keywords: chromophores; dyes/pigments; fluorescence; imaging; photophysics