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RESEARCH PRODUCT
Synthesis of new asymmetric xanthene dyes via catalyst-free SNAr with sulfur nucleophiles
Mark HelmMichaela KotaskovaOkan Osman Oglousubject
XantheneAzidesOrganic Chemistrychemistry.chemical_elementElectronsHydrogen-Ion ConcentrationSulfidesPhotochemistryBiochemistrySulfurCombinatorial chemistryCatalysisCatalysischemistry.chemical_compoundSpectrometry FluorescenceXantheneschemistryNucleophileNucleophilic aromatic substitutionMoietyPhysical and Theoretical ChemistrySulfurFluorescent DyesMacromoleculedescription
Addition of a single functional handle to the tricyclic moiety of fluorescein results in asymmetric xanthene dyes. Our synthesis of a new class of asymmetric xanthenes proceeds via an unusual SNAr with sulfur nucleophiles on electron rich aromatic xanthenes scaffolds in the absence of a metal catalyst. The resulting 3'-thioethers exhibit high photostability and are conveniently converted into reactive dyes for macromolecule labelling.
year | journal | country | edition | language |
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2014-05-08 | Organic & Biomolecular Chemistry |