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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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Article information


Submitted
15 Feb 2019
Accepted
20 Apr 2019
First published
23 Apr 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5405-5422
Article type
Edge Article

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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