Rigid urea and self-healing thiourea ethanolamine monolayers

Stefaniu, Cristina; Zaffalon, Pierre-Léonard; Carmine, Alessio; Verolet, Quentin; Fernandez, Samuel; Wesolowski, Tomasz A.; Brezesinski, Gerald; Zumbuehl, Andreas

doi:10.1021/la5039987

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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

03.02.2015

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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

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