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Synthesis and optical properties of water-soluble diketopyrrolopyrroles

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Chemistry of Heterocyclic Compounds Aims and scope

Two diketopyrrolopyrroles containing electron-rich 3,4-dimethoxyphenyl and 2-furyl aromatic groups were decorated with N-alkyl substituents containing quaternary ammonium moieties. The obtained dyes were readily soluble in water, showed an intense visible absorption with relatively high two-photon absorption cross-sections and some of them could stain eukaryotic cells. A dye containing two tetraalkylammonium moieties in its side chains showed high fluorescence quantum yield (>50%) both in water and in acetonitrile, whereas the fluorescence of pyridinium salt was significantly quenched. The two-photon absorption peaks were located at ~720 nm.

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The financial support by Polish National Science Centre (MAESTRO-2012/06/A/ST5/00216) and the Conseil Régional d’Aquitaine for (Chaire d’accueil grant and fellowship to VH) is gratefully acknowledged. This work was partially supported by the European Commission (TOPBIO ITN).

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Authors and Affiliations

  1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland

    Marek Grzybowski & Daniel T. Gryko

  2. Department of Laboratory Diagnostics and Clinical Immunology of Developmental Age, Medical University of Warsaw, Marszałkowska 24, 00-576, Warsaw, Poland

    Eliza Glodkowska-Mrowka

  3. Institut des Sciences Moléculaires, Université de Bordeaux (CNRS UMR 5255), A12 Bâtiment, 351 cours de la Libération, 33405, Talance Cedex, France

    Guillame Clermont & Mireille Blanchard-Desce

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  1. Marek Grzybowski
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  2. Eliza Glodkowska-Mrowka
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  3. Guillame Clermont
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  4. Mireille Blanchard-Desce
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  5. Daniel T. Gryko
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Correspondence to Mireille Blanchard-Desce or Daniel T. Gryko.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 72–77

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Grzybowski, M., Glodkowska-Mrowka, E., Clermont, G. et al. Synthesis and optical properties of water-soluble diketopyrrolopyrroles. Chem Heterocycl Comp 53, 72–77 (2017). https://doi.org/10.1007/s10593-017-2023-y

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  • DOI: https://doi.org/10.1007/s10593-017-2023-y

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