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  Functionalization of the meso-phenyl ring of rhodamine dyes through SNAr with sulfur nucleophiles: Synthesis, biophysical characterizations, and comprehensive NMR analysis.

Mitronova, G., Polyakova, S., Wurm, C. A., Kolmakov, K., Wolfram, T., Meineke, D. N. H., et al. (2015). Functionalization of the meso-phenyl ring of rhodamine dyes through SNAr with sulfur nucleophiles: Synthesis, biophysical characterizations, and comprehensive NMR analysis. European Journal of Organic Chemistry, 2015(2), 337-349. doi:10.1002/ejoc.201403269.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0024-ADAB-7 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-F687-7
Genre: Journal Article

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 Creators:
Mitronova, G.1, Author              
Polyakova, S.1, Author              
Wurm, C. A.1, Author              
Kolmakov, K.1, Author              
Wolfram, T., Author
Meineke, D. N. H.1, Author              
Belov, V. N.1, Author              
John, M., Author
Hell, S. W.1, Author              
Affiliations:
1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              

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Free keywords: Dyes/Pigments; Fluorescence; Structure elucidation; NMR spectroscopy; Optical microscopy
 Abstract: Aromatic nucleophilic substitution (SNAr) of fluorine in 9-(3′-carboxy-4′,5′,6′,7′-tetrafluorophenyl) groups of xanthene dyes constitutes a powerful tool in dye design. Thiols and amines regioselectively replace F-6′. This approach enables additional hydrophilic residues or functional groups required for bioconjugation to be introduced. By using this methodology, a “bright” and photostable dye for two-color superresolution microscopy was synthesized (with absorption and emission maxima at 604 and 627 nm, respectively). In the case of red-emitting rhodamine dyes with 3′-carboxy-4′,5′,7′-trifluorophenyl residues, two-dimensional NMR techniques and a chemical transformation were used to prove the precise position of the additional substituent – a carboxylic acid group linked through the S-atom at C-6′. Furthermore, simple 1H NMR spectra reliably permit the position of the additional carboxy substituent in the 3′-carboxyphenyl ring (at C-5′ or C-6′) to be established. Information on the exact position of this substituent is significant for the design of molecular probes and for the prediction of the properties of their bioconjugates.

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Language(s): eng - English
 Dates: 2014-11-262015-01
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/ejoc.201403269
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Title: European Journal of Organic Chemistry
Source Genre: Journal
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Pages: - Volume / Issue: 2015 (2) Sequence Number: - Start / End Page: 337 - 349 Identifier: -