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Direct Olefination of Fluorinated Quinoxalines <i>via</i> Cross‐ Dehydrogenative Coupling Reactions: A New Near‐Infrared Probe for Mitochondria
15
Citations
104
References
2017
Year
Bioorganic ChemistryEngineeringOrganic ChemistryChemistryLarge LibraryPhosphorescence ImagingLarge Stokes ShiftsReaction IntermediateBioimagingPhotophysical PropertyMolecular ImagingQuinoxaline FluorophoresCross-coupling ReactionBiochemistryPhotochemistryFluorous SynthesisBiophotonicsBiomolecular EngineeringNatural SciencesDirect OlefinationNew Near‐infrared Probe
Abstract A large library of 5,8‐distyrylquinoxaline fluorophores was synthesized in good‐to‐excellent yields via a palladium‐catalyzed oxidative C–H/C–H cross‐coupling of electron‐deficient fluorinated quinoxalines with electron‐rich styrenes. The resulting quinoxaline fluorophores (Qu‐Fluors) exhibited tunable color emissions with the quantum yields of up to 83% and large Stokes shifts of up to 6236 cm −1 in dichloromethane. The bioimaging performance of the Qu‐Fluors was shown to have potential as near‐infrared fluorescent probes for mitochondria. magnified image
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