Unprecedented perspectives on the application of CinNapht fluorophores provided by a "late-stage" functionalization strategy

A simple and easy-to-implement process based on a nucleophilic aromatic substitution reaction with a wide variety of nucleophiles on a fluorinated CinNapht is described. This process has the key advantage of introducing multiple functionalities at a very late stage, thus providing access to new appl...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2023-06, Vol.14 (22), p.6-61
Main Authors: Tacke, Eléonore, Hoang, Minh-Duc, Tatoueix, Kevin, Keromnes, Benoît, Van Eslande, Elsa, Durand, Philippe, Pieters, Gregory, Chevalier, Arnaud
Format: Article
Language:English
Subjects:
Chemical compounds
Chemical Sciences
Chemical synthesis
Chemistry
Imaging
Lipids
Nucleophiles
Signal to noise ratio
Substitution reactions
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Summary:A simple and easy-to-implement process based on a nucleophilic aromatic substitution reaction with a wide variety of nucleophiles on a fluorinated CinNapht is described. This process has the key advantage of introducing multiple functionalities at a very late stage, thus providing access to new applications including the synthesis of photostable and bioconjugatable large Stokes shift red emitting dyes and selective organelle imaging agents, as well as AIEE-based wash-free lipid droplet imaging in live cells with high signal-to-noise ratio. The synthesis of bench-stable CinNapht-F has been optimized and can be reproduced on a large scale, making it an easy-to-store starting material that can be used at will to prepare new molecular imaging tools. A simple and easy-to-implement process based on a nucleophilic aromatic substitution reaction with a wide variety of nucleophiles on a fluorinated CinNapht offers unprecedented perspectives.
ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc01365k