Significance of the Amide Functionality on DOPA-Based Monolayers on Gold

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 detai...

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Bibliographic Details
Published in:Langmuir 2012-12, Vol.28 (49), p.16900-16908
Main Authors: Rı̅bena, Dina, Alekseev, Alexander, van Asselen, Otto, Mannie, Gilbère J. A, Hendrix, Marco M. R. M, van der Ven, Leendert G. J, Sommerdijk, Nico A. J. M, de With, Gijsbertus
Format: Article
Language:English
Subjects:
Adhesives - chemistry
Amides - chemistry
Animals
Biomimetic Materials - chemistry
Bivalvia - chemistry
Catechols - chemistry
Chemistry
Crystallization
Dihydroxyphenylalanine - chemistry
Dopamine - analogs & derivatives
Dopamine - chemistry
Exact sciences and technology
General and physical chemistry
Gold - chemistry
Langmuir blodgett films
Microscopy, Atomic Force
Photoelectron Spectroscopy
Proteins - chemistry
Solid-liquid interface
Spectrophotometry, Infrared
Spectrum Analysis, Raman
Stearates - chemistry
Surface physical chemistry
Surface Properties
Thermodynamics
Water - chemistry
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Summary: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.
ISSN:0743-7463
1520-5827
DOI:10.1021/la303308m