Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells12. Issue 20 (2nd May 2019)

• Record Type: Journal Article
• Authors: Griesbeck, Stefanie; Michail, Evripidis; Wang, Chenguang; Ogasawara, Hiroaki; Lorenzen, Sabine; Gerstner, Lukas; Zang, Theresa; Nitsch, Jörn; Sato, Yoshikatsu; Bertermann, Rüdiger; Taki, Masayasu; Lambert, Christoph; Yamaguchi, Shigehiro; Marder, Todd B.
• Is Part Of: Chemical science. Volume 10:Issue 20(2019)
• Page Start: 5405
• Page End: 5422
• Publication Date: 2019-05-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc00793h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The tetracationic diketopyrrolopyrrole compound5M exhibits a σ 2 value of 4560 GM at 740 nm. 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 precursors1–5 displayed highly solvatochromic fluorescence, the water-soluble tetracationic target molecules1M–5M, did not, but their emission colour could be tuned from blue to pink by changing the π-bridge. Compound5M, 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 of5M combined with two-photon excited fluorescence imaging studies demonstrate its excellent potential for lysosomal imaging in live cells.