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Rigid urea and self-healing thiourea ethanolamine monolayers.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2015
Author Stefaniu Cristina, Zaffalon Pierre-Léonard, Carmine Alessio, Verolet Quentin, Fernandez Samuel, Wesolowski Tomasz A, Brezesinski Gerald, Zumbuehl Andreas,
Project Approaches for Non-spherical and Surface Activated Liposomes
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Original article (peer-reviewed)

Journal Langmuir : the ACS journal of surfaces and colloids
Volume (Issue) 31(4)
Page(s) 1296 - 302
Title of proceedings Langmuir : the ACS journal of surfaces and colloids
DOI 10.1021/la5039987


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.