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Issue 20, 2019
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Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

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Abstract

A series of tetracationic quadrupolar chromophores containing three-coordinate boron π-acceptors linked by different π-bridges, namely 4,4′-biphenyl, 2,7-pyrene, 2,7-fluorene, 3,6-carbazole and 5,5′-di(thien-2-yl)-3,6-diketopyrrolopyrrole, were synthesized. While their neutral precursors 1–5 displayed highly solvatochromic fluorescence, the water-soluble tetracationic target molecules 1M–5M, did not, but their emission colour could be tuned from blue to pink by changing the π-bridge. Compound 5M, containing the diketopyrrolopyrrole bridge, exhibits the most red-shifted absorption and emission maxima and the largest two-photon absorption cross-section (4560 GM at 740 nm in MeCN). Confocal laser scanning fluorescence microscopy studies in live cells confirm localization of the dye at the lysosome. Moreover, the low cytotoxicity, and high photostability of 5M combined with two-photon excited fluorescence imaging studies demonstrate its excellent potential for lysosomal imaging in live cells.

Graphical abstract: Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

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Publication details

The article was received on 15 Feb 2019, accepted on 20 Apr 2019 and first published on 23 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC00793H
Chem. Sci., 2019,10, 5405-5422
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

    S. Griesbeck, E. Michail, C. Wang, H. Ogasawara, S. Lorenzen, L. Gerstner, T. Zang, J. Nitsch, Y. Sato, R. Bertermann, M. Taki, C. Lambert, S. Yamaguchi and T. B. Marder, Chem. Sci., 2019, 10, 5405
    DOI: 10.1039/C9SC00793H

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