6533b85afe1ef96bd12b95d8

RESEARCH PRODUCT

Straightforward access to water-soluble unsymmetrical sulfoxanthene dyes: application to the preparation of far-red fluorescent dyes with large stokes' shifts.

Anthony RomieuAnthony RomieuPierre-yves RenardArnaud Chevalier

subject

[CHIM.THER]Chemical Sciences/Medicinal ChemistryBiosensing Techniques010402 general chemistryPhotochemistry01 natural sciencesCatalysisRhodaminessymbols.namesakechemistry.chemical_compoundAniline[CHIM.ANAL]Chemical Sciences/Analytical chemistryCoumarinsStokes shiftMoietyJulolidineComputingMilieux_MISCELLANEOUSFluorescent DyesAqueous solution010405 organic chemistryChemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryRhodaminesOrganic ChemistryWaterGeneral Chemistry[CHIM.CATA]Chemical Sciences/CatalysisHydrogen-Ion ConcentrationFluorescence0104 chemical sciences[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistrySpectrometry FluorescenceXanthenessymbolsSolventsBiosensor[CHIM.CHEM]Chemical Sciences/Cheminformatics

description

An efficient synthesis of water-soluble unsymmetrical sulforhodamine/sulforhodol fluorophores containing a single julolidine fragment is presented. Owing to their valuable spectral properties in aqueous buffers, these dyes, especially those bearing a free aniline or phenol moiety, are valuable components of fluorogenic probes for a variety of biosensing applications. A further extension of this synthetic methodology to unusual phenols, namely 7-N,N-dialkylamino-4-hydroxy coumarins has enabled us to provide a new family water-soluble dyes of large Stokes’ shift with far-red spectral features.

10.1002/chem.201402306https://pubmed.ncbi.nlm.nih.gov/24863167