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Issue 8, 2017
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The para-fluoro-thiol ligation in water

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Abstract

The para-fluoro-thiol reaction (PFTR) is performed for the first time in aqueous media. A water-soluble model scaffold based on poly(N,N-dimethylacrylamide) and incorporating pentafluorostyrene units was synthesized by nitroxide-mediated copolymerization. The effect of pH, temperature, and stoichiometry on the solution-phase kinetics of the PFTR for side-chain modification is studied by 19F and 1H NMR spectroscopy using mercaptoethanol as a model thiol. While the reaction can occur from pH 11 on, increasing pH greatly accelerates the reaction. Yields >90% are achieved at pH 12 and 40 °C in 24 h, while quantitative coupling is reached at pH 13 and 50 °C in less than 16 h. Grafting of a cysteine-containing peptide on tissue culture plates demonstrated by ToF-SIMS evidences the benefit of performing this reaction in aqueous media for surface functionalization of materials prone to degradation in organic solvents.

Graphical abstract: The para-fluoro-thiol ligation in water

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Publication details

The article was received on 07 Dec 2016, accepted on 12 Jan 2017 and first published on 16 Jan 2017


Article type: Communication
DOI: 10.1039/C6PY02108E
Citation: Polym. Chem., 2017,8, 1288-1293
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    The para-fluoro-thiol ligation in water

    H. Turgut, A. C. Schmidt, P. Wadhwani, A. Welle, R. Müller and G. Delaittre, Polym. Chem., 2017, 8, 1288
    DOI: 10.1039/C6PY02108E

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