Optimization of Aqueous Stability versus π-Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live-Cell Fluorescence Imaging |
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| Authors: | Stefanie Griesbeck Matthias Ferger Corinna Czernetzi Dr Chenguang Wang Dr Rüdiger Bertermann Dr Alexandra Friedrich Dr Martin Haehnel Dr Daniel Sieh Dr Masayasu Taki Prof Dr Shigehiro Yamaguchi Prof Dr Todd B Marder |
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| Institution: | 1. Institut für Anorganische Chemie, Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, 97074 Würzburg, Germany;2. Institute of Transformative Bio-Molecules, Nagoya University, Nagoya, Japan |
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| Abstract: | The stability of tetracationic triarylboranes in dilute aqueous solution was investigated by tuning the steric demand of the linker in a (para-(N,N,N-trimethylammonio)xylyl)2B–(linker)–B(para-(N,N,N-trimethylammonio)xylyl)2 structure. With increasing steric bulk of the linker, namely 1,4-phenylene, 2,2′′′-(3,3′′′-dimethyl)-5,2′:5′,2′′:5′′,5′′′-quaterthiophene, 9,10-anthracenylene, and 4,4′′′-(5′-(3,5-dimethylphenyl))(5′′-(3′′′,5′′′-dimethylphenyl))-2′,2′′-bithiophene, the stability of the compounds increased. The anthracene-based chromophore, compound 3M is water-stable for at least 48 h, is nontoxic to cells and exhibits an exceedingly high fluorescence quantum yield of 0.86 in water making it an ideal candidate for confocal live-cell imaging of lysosomes. |
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| Keywords: | boranes boron fluorescence imaging luminescence |
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