Journal article
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Rigid urea and self-healing thiourea ethanolamine monolayers
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Stefaniu, Cristina
Max Planck Institute of Colloids and Interfaces, Potsdam, Germany
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Zaffalon, Pierre-Léonard
Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, University of Geneva, Switzerland
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Carmine, Alessio
Department of Physical Chemistry, University of Geneva, Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland
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Verolet, Quentin
Department of Chemistry, University of Fribourg, Chemin du Musée 9, 1700 Fribourg, Switzerland
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Fernandez, Samuel
Department of Chemistry, University of Fribourg, Switzerland - National Centre of Competence in Research in Chemical Biology, University of Geneva, Switzerland
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Wesolowski, Tomasz A.
Department of Physical Chemistry, University of Geneva, Switzerland
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Brezesinski, Gerald
Max Planck Institute of Colloids and Interfaces, Potsdam, Germany
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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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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.
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Faculty
- Faculté des sciences et de médecine
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Department
- Département de Chimie
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Language
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Classification
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Chemistry
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License
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License undefined
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Identifiers
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Persistent URL
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https://folia.unifr.ch/unifr/documents/304428
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