Issue 20, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Febr. 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
Creative Commons BY-NC license

Chem. Sci., 2019,10, 5405-5422

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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