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 journalArticle

12 Citations (Scopus)

Abstract

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
JournalLangmuir
Volume28
Issue number49
DOIs
Publication statusPublished - Dec 11 2012
Externally publishedYes

Fingerprint

dopa
Dihydroxyphenylalanine
Amides
Gold
amides
Monolayers
gold
adhesives
Adhesives
glues
infrared reflection
amino acids
Glues
oxygen atoms
absorption spectroscopy
plastics
Angle measurement
Raman spectroscopy
Absorption spectroscopy
photoelectron spectroscopy

ASJC Scopus subject areas

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

Cite this

Ribena, D., Alekseev, A., Van Asselen, O., Mannie, G. J. A., Hendrix, M. M. R. M., Van Der Ven, L. G. J., ... De With, G. (2012). Significance of the amide functionality on DOPA-based monolayers on gold. Langmuir, 28(49), 16900-16908. https://doi.org/10.1021/la303308m

Significance of the amide functionality on DOPA-based monolayers on gold. / Ribena, 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.

In: Langmuir, Vol. 28, No. 49, 11.12.2012, p. 16900-16908.

Research output: Contribution to journalArticle

Ribena, D, Alekseev, A, Van Asselen, O, Mannie, GJA, Hendrix, MMRM, Van Der Ven, LGJ, Sommerdijk, NAJM & De With, G 2012, 'Significance of the amide functionality on DOPA-based monolayers on gold', Langmuir, vol. 28, no. 49, pp. 16900-16908. https://doi.org/10.1021/la303308m
Ribena D, Alekseev A, Van Asselen O, Mannie GJA, Hendrix MMRM, Van Der Ven LGJ et al. Significance of the amide functionality on DOPA-based monolayers on gold. Langmuir. 2012 Dec 11;28(49):16900-16908. https://doi.org/10.1021/la303308m
Ribena, 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. / Significance of the amide functionality on DOPA-based monolayers on gold. In: Langmuir. 2012 ; Vol. 28, No. 49. pp. 16900-16908.
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