title: Synthesis of new asymmetric xanthene dyes via catalyst-free S(N)Ar with sulfur nucleophiles.
abstract: 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.
authors.affiliation: Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University Mainz, Staudingerweg 5, D-55128 Mainz, Germany. mhelm@uni-mainz.de.
authors.forename: Michaela
authors.initials: M
authors.lastname: Kotaskova
authors.forename: Okan Osman
authors.initials: OO
authors.lastname: Oglou
authors.forename: Mark
authors.initials: M
authors.lastname: Helm
mesh_terms: D001386:Azides / Q000737:chemistry; D002384:Catalysis; D004583:Electrons; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D013050:Spectrometry, Fluorescence; D013440:Sulfides / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001386:Azides; D005456:Fluorescent Dyes; D013440:Sulfides; D014966:Xanthenes; D013455:Sulfur