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Rigid Urea and Self-Healing Thiourea Ethanolamine Monolayers

Stefaniu, Cristina
Zaffalon, Pierre-Léonard
Fernandez, Samuel
Brezesinski, Gerald
Published in Langmuir. 2015, vol. 31, no. 4, p. 1296-1302
Abstract 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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Research group Groupe Wesolowski
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STEFANIU, Cristina et al. Rigid Urea and Self-Healing Thiourea Ethanolamine Monolayers. In: Langmuir, 2015, vol. 31, n° 4, p. 1296-1302. doi: 10.1021/la5039987 https://archive-ouverte.unige.ch/unige:55058

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Deposited on : 2015-04-01

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