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Optimization of Aqueous Stability versus π‐Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live‐Cell Fluorescence Imaging
Author(s) -
Griesbeck Stefanie,
Ferger Matthias,
Czernetzi Corinna,
Wang Chenguang,
Bertermann Rüdiger,
Friedrich Alexandra,
Haehnel Martin,
Sieh Daniel,
Taki Masayasu,
Yamaguchi Shigehiro,
Marder Todd B.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900723
Subject(s) - chromophore , linker , steric effects , fluorescence , anthracene , quantum yield , aqueous solution , chemistry , phenylene , photochemistry , stereochemistry , polymer , organic chemistry , optics , physics , computer science , operating system
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) 2 B–(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.