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Rigid urea and self-healing thiourea ethanolamine monolayers

  • Stefaniu, Cristina Max Planck Institute of Colloids and Interfaces, Potsdam, Germany
  • Zaffalon, Pierre-Léonard Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, University of Geneva, Switzerland
  • Carmine, Alessio Department of Physical Chemistry, University of Geneva, Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland
  • Verolet, Quentin Department of Chemistry, University of Fribourg, Chemin du Musée 9, 1700 Fribourg, Switzerland
  • Fernandez, Samuel Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, University of Geneva, Switzerland
  • Wesolowski, Tomasz A. Department of Physical Chemistry, University of Geneva, Switzerland
  • Brezesinski, Gerald Max Planck Institute of Colloids and Interfaces, Potsdam, Germany
  • Zumbuehl, Andreas Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, University of Geneva, Switzerland
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    03.02.2015
Published in:
  • Langmuir. - 2015, vol. 31, no. 4, p. 1296–1302
English A series of long-tail alkyl ethanolamine analogs containing amide-, urea-, and thiourea moieties was synthesized and the behavior of the corresponding monolayers was assessed on the Langmuir–Pockels trough combined with grazing incidence X-ray diffraction experiments and complemented by computer simulations. All compounds form stable monolayers at the soft air/water interface. The phase behavior is dominated by strong intermolecular headgroup hydrogen bond networks. While the amide analog forms well-defined monolayer structures, the stronger hydrogen bonds in the urea analogs lead to the formation of small three-dimensional crystallites already during spreading due to concentration fluctuations. The hydrogen bonds in the thiourea case form a two-dimensional network, which ruptures temporarily during compression and is recovered in a self-healing process, while in the urea clusters the hydrogen bonds form a more planar framework with gliding planes keeping the structure intact during compression. Because the thiourea analogs are able to self-heal after rupture, such compounds could have interesting properties as tight, ordered, and self-healing monolayers.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/304428
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