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Photophysics of New Photostable Rylene Derivatives: Applications in Single-Molecule Studies and Membrane Labelling

Authors

  • Melari Davies,

    1. Department of Chemistry and Center for Nanoscience (CeNS), Ludwig-Maximilians-Universität München, Butenandtstrasse 11, 81377 München (Germany), Fax: (+49) 89-2180-77548
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  • Dr. Christophe Jung,

    1. Department of Chemistry and Center for Nanoscience (CeNS), Ludwig-Maximilians-Universität München, Butenandtstrasse 11, 81377 München (Germany), Fax: (+49) 89-2180-77548
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  • Philipp Wallis,

    1. Department of Chemistry and Center for Nanoscience (CeNS), Ludwig-Maximilians-Universität München, Butenandtstrasse 11, 81377 München (Germany), Fax: (+49) 89-2180-77548
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  • Tobias Schnitzler,

    1. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany)
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  • Dr. Chen Li,

    1. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany)
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  • Prof. Dr. Klaus Müllen,

    1. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany)
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  • Prof. Dr. Christoph Bräuchle

    Corresponding author
    1. Department of Chemistry and Center for Nanoscience (CeNS), Ludwig-Maximilians-Universität München, Butenandtstrasse 11, 81377 München (Germany), Fax: (+49) 89-2180-77548
    • Department of Chemistry and Center for Nanoscience (CeNS), Ludwig-Maximilians-Universität München, Butenandtstrasse 11, 81377 München (Germany), Fax: (+49) 89-2180-77548
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Abstract

Three new photostable rylene dyes for applications in single molecule studies and membrane labelling have been synthesized and their photophysical properties were characterized. These dyes differ in the number of polyethylene glycol (PEG) chains attached to the core structure which is either a perylene derivate or a terrylene derivate. One perylene and one terrylene dye is modified with two PEG chains, and another terrylene derivate has four PEG chains. The results show that the terrylene dye with four PEG chains (4-PEG-TDI) forms soluble nonfluorescing H-aggregates in water, so that the absorption bands are blue-shifted with respect to those of the fluorescing monomeric form. The presence of a surfactant such as Pluronic P123 leads to the disruption of the aggregates due to the formation of monomers in micelles and a strong increase in fluorescence. Application for labelling cell membranes can be considered for this dye since it adsorbs in a similar way as monomer to a lipid bilayer. Furthermore a single-molecule study of all three rylene dyes in polymeric films of PMMA showed excellent photostability with respect to photobleaching, far above the photostability of other common water-soluble dyes, such as Oxazine-1, Atto647N, Cy5, Alexa647 and Rhodamin6G. Especially 4-PEG-TDI seems to be a promising dye for membrane labelling with its high photostability.

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