6533b821fe1ef96bd127c416

RESEARCH PRODUCT

Synthesis of new asymmetric xanthene dyes via catalyst-free SNAr with sulfur nucleophiles

Mark HelmMichaela KotaskovaOkan Osman Oglou

subject

XantheneAzidesOrganic Chemistrychemistry.chemical_elementElectronsHydrogen-Ion ConcentrationSulfidesPhotochemistryBiochemistrySulfurCombinatorial chemistryCatalysisCatalysischemistry.chemical_compoundSpectrometry FluorescenceXantheneschemistryNucleophileNucleophilic aromatic substitutionMoietyPhysical and Theoretical ChemistrySulfurFluorescent DyesMacromolecule

description

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.

https://doi.org/10.1039/c4ob00533c