Reservible covalent patterning of self-assembled monolayers on gold an silicon oxide surfaces

D.I. Rozkiewicz, B.J. Ravoo, David Reinhoudt

    Research output: Contribution to journalArticleAcademicpeer-review

    80 Citations (Scopus)


    This paper describes the generation of reversible patterns of self-assembled monolayers (SAMs) on gold and silicon oxide surfaces via the formation of reversible covalent bonds. The reactions of (patterned) SAMs of 11-amino-1-undecanethiol (11-AUT) with propanal, pentanal, decanal, or terephthaldialdehyde result in dense imine monolayers. The regeneration of these imine monolayers to the 11-AUT monolayer is obtained by hydrolysis at pH 3. The (patterned) monolayers were characterized by Fourier transform infrared reflection absorption spectroscopy, X-ray photoelectron spectroscopy, contact angle and electrochemical measurements, and atomic force microscopy. Imines can also be formed by microcontact printing of amines on terephthaldialdehyde-terminated substrates. Lucifer Yellow ethylenediamine was employed as a fluorescent amine-containing marker to visualize the reversible covalent patterning on a terephthaldialdehyde-terminated glass surface by confocal microscopy. These experiments demonstrate that with reversible covalent chemistry it is possible to print and erase chemical patterns on surfaces repeatedly.
    Original languageUndefined
    Pages (from-to)7866-7876
    Issue number14
    Publication statusPublished - 2005


    • IR-53010
    • METIS-225116

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