Significance of the amide functionality on DOPA-based monolayers on gold

Dina Ribena, Alexander Alekseev, Otto Van Asselen, Gilbère J.A. Mannie, Marco M.R.M. Hendrix, Leendert G.J. Van Der Ven, Nico A.J.M. Sommerdijk, Gijsbertus De With

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)


    The adhesive proteins secreted by marine mussels contain an unusual amino acid, 3,4-dihydroxyphenylalanine (DOPA), that is responsible for the cohesive and adhesive strength of this natural glue and gives mussels the ability to attach themselves to rocks, metals, and plastics. Here we report a detailed structural and spectroscopic investigation of the interface between N-stearoyldopamine and a single-crystalline Au(111) model surface and an amide-absent molecule, 4-stearylcatechol, also on Au(111), with the aim of understanding the role of the amide functionality in the packing, orientation, and fundamental interaction between the substrate and the monolayer formed from an aqueous environment by the Langmuir-Blodgett technique. The organization of monolayers on gold was observed directly and studied in detail by X-ray photoelectron spectroscopy (XPS), contact angle measurements (CA), surface-enhanced Raman spectroscopy (SERS), infrared reflection-absorption spectroscopy (IRRAS), and atomic force microscopy (AFM). Our study shows that within the monolayer the catecholic oxygen atoms are coordinated to the gold surface, having a more perpendicular orientation with respect to the aromatic ring and the apparently tilted alkyl chains, whereas the amide functionality stabilizes the monolayer that is formed.

    Original languageEnglish
    Pages (from-to)16900-16908
    Number of pages9
    Issue number49
    Publication statusPublished - Dec 11 2012

    ASJC Scopus subject areas

    • Materials Science(all)
    • Condensed Matter Physics
    • Surfaces and Interfaces
    • Spectroscopy
    • Electrochemistry


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