Straightforward Access to Water-Soluble Unsymmetrical Sulfoxanthene Dyes: Application to the Preparation of Far-Red Fluorescent Dyes with Large Stokes' Shifts

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 compo...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-07, Vol.20 (27), p.8330-8337
Main Authors: Chevalier, Arnaud, Renard, Pierre-Yves, Romieu, Anthony
Format: Article
Language:English
Subjects:
Analytical chemistry
Biosensing Techniques
Catalysis
Chemical Sciences
Cheminformatics
Chemistry
Coumarin
Coumarins - chemical synthesis
Coumarins - chemistry
Dyes
far-red dyes
Fluid flow
Fluorescence
Fluorescent dyes
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
fluorescent probes
Fragmentation
Hydrogen-Ion Concentration
Medicinal Chemistry
or physical chemistry
Organic chemistry
Phenol
rhodamines
Rhodamines - chemical synthesis
Rhodamines - chemistry
rhodols
Solvents - chemistry
Spectra
Spectrometry, Fluorescence
Stokes' shift
Theoretical and
Water - chemistry
Xanthenes - chemistry
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Summary: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. Unity is strength! A concise and efficient synthetic route toward unsymmetrical sulforhodamine/sulforhodol dyes has been developed (see scheme). Ten different fluorophores both soluble and fluorescent in polar organic solvents and in aqueous media were obtained. Those with a fused coumarin fragment are a novel class of far‐red fluorescent dyes with attractive spectral features especially for use under physiological conditions.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201402306