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Photoactivatable Fluorogens by Intramolecular C-H Insertion of Perfluoroaryl Azide.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Nov 15; Vol. 84 (22), pp. 14520-14528. Date of Electronic Publication: 2019 Oct 29. - Publication Year :
- 2019
-
Abstract
- Molecules, capable of fluorescence turn-on by light, are highly sought-after in spatio-temporal labeling, surface patterning, monitoring cellular and molecular events, and high-resolution fluorescence imaging. In this work, we report a fluorescence turn-on system based on photoinitiated intramolecular C-H insertion of azide into the neighboring aromatic ring. The azide-masked fluorogens were efficiently synthesized via a cascade nucleophilic aromatic substitution of perfluoroaryl azides with carbazoles. The scaffold also allows for derivatization with biological ligands, as exemplified with d-mannose in this study. This photoinitiated intramolecular transformation led to high yields, high photo-conversion efficiency, and well-separated wavelengths for photoactivation and fluorescence excitation. The mannose-derivatized structure enabled spatio-temporal activation and showed high contrast and signal amplification. Live cell imaging suggested that the mannose-tagged fluorogen was transported to the lysosomes.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 22
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31589042
- Full Text :
- https://doi.org/10.1021/acs.joc.9b02050