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Direct UV-Induced Functionalization of Surface Hydroxy Groups by Thiol–Ol Chemistry

Authors

  • Linxian Li,

    1. Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany)
    2. Department of Organic Chemistry, University of Heidelberg (Germany)
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    • These authors contributed equally to this work.

  • Junsheng Li,

    1. Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany)
    2. Department of Applied Physical Chemistry, University of Heidelberg (Germany)
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    • These authors contributed equally to this work.

  • Xin Du,

    1. Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany)
    2. Department of Applied Physical Chemistry, University of Heidelberg (Germany)
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  • Dr. Alexander Welle,

    1. Institute of Functional Interfaces (IFG), KIT (Germany)
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  • Prof. Dr. Michael Grunze,

    1. Institute of Functional Interfaces (IFG), KIT (Germany)
    2. Department of Applied Physical Chemistry, University of Heidelberg (Germany)
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  • Prof. Dr. Oliver Trapp,

    1. Department of Organic Chemistry, University of Heidelberg (Germany)
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  • Dr. Pavel A. Levkin

    Corresponding author
    1. Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany)
    2. Department of Organic Chemistry, University of Heidelberg (Germany)
    • Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany)http://www.levkingroup.com===

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  • This work was funded by the Helmholtz Association’s Initiative and Networking Fund (grant VH-NG-621). We thank Hao Lv (APC, Heidelberg) and Chengwu Yang (IFG, KIT) for help for the XPS measurements. J. Li and X. Du thank China Scholarship Council for PhD scholarships.

Abstract

A novel UV-initiated surface modification method for the direct functionalization of surface hydroxy groups with thiol-containing molecules (termed “thiol–ol” modification) is described. This method is based on the oxidative conjugation of thiols to hydroxy groups. We demonstrate that different thiol-containing molecules, such as fluorophores, thiol-terminated poly(ethylene glycol) (PEG-SH), and a cysteine-containing peptide, can be attached onto the surface of porous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate). Direct functionalization of other hydroxy-group-bearing surfaces, fabrication of micropatterns, and double patterning have been also demonstrated using the thiol–ol method.

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