Rigid Urea and Self-Healing Thiourea Ethanolamine Monolayers

Article Article scientifique Article Rigid Urea and Self-Healing Thiourea Ethanolamine Monolayers eng 2015 author Stefaniu Cristina author Zaffalon Pierre-Léonard author Carmine Alessio 669780 author Verolet Quentin 658847 author Fernandez Samuel 641097 author Wesolowski Tomasz Adam 92358 author Brezesinski Gerald author Zumbuehl Andréas 668486 1296-1302 10.1021/la5039987 0743-7463 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. Dewey 540 36 Département de chimie organique 141 38 Département de chimie physique 142 false 689 Groupe Wesolowski Langmuir 31 4 f65a51b1-5578-4b22-a5ed-4b22af979b8c Article (Published version) Restricted ref01458.pdf 358906 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique Faculté des sciences / Section de chimie et biochimie / Département de chimie physique

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Rigid Urea and Self-Healing Thiourea Ethanolamine Monolayers	Langmuir			2015	689	1

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Fernandez, Samuel