1193501-29-9Relevant academic research and scientific papers
Synthesis of azido-substituted benzaldehydes via SNAr chemistry
Kafle, Arjun,Yossef, Sandy,Handy, Scott T.
supporting information, (2020/04/21)
Conditions for the formation of azidobenzaldehydes and azidobenzonitriles using sodium azide in DMSO under typical SNAr conditions are described. This simplifies access to these valuable building blocks compared to the more common sequences reported in the literature. Interestingly, fluorosubstituted aryl ketones and esters do not afford azides, but instead amine products.
Azido push-pull fluorogens photoactivate to produce bright fluorescent labels
Lord, Samuel J.,Lee, Hsiao-Lu D.,Samuel, Reichel,Weber, Ryan,Liu, Na,Conley, Nicholas R.,Thompson, Michael A.,Twieg, Robert J.,Moerner
experimental part, p. 14157 - 14167 (2011/04/24)
Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging. Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine, thus restoring charge-transfer absorption and fluorescence. Previously, we reported that one compound, DCDHF-V-P-azide, was photoactivatable. Here, we demonstrate that the azide-to-amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield, photostability, and turn-on ratio. Azido push-pull fluorogens provide a new class of photoactivatable singlemolecule probes for fluorescent labeling and super-resolution microscopy. Lastly, we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling).
