Stefaniu, Cristina Zaffalon, Pierre-Léonard Carmine, Alessio Verolet, Quentin Fernandez, Samuel Wesolowski, Tomasz A. Brezesinski, Gerald Zumbuehl, Andreas 2015-02-03 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. application/pdf https://folia.unifr.ch/global/documents/304428 https://folia.unifr.ch/documents/304428/files/zum_rus.pdf https://folia.unifr.ch/documents/304428/files/zum_rus_sm.pdf eng info:eu-repo/semantics/altIdentifier/doi/10.1021/la5039987 info:eu-repo/semantics/openAccess License undefined Langmuir. - 2015, vol. 31, no. 4, p. 1296–1302 info:eu-repo/classification/udc/54 Rigid urea and self-healing thiourea ethanolamine monolayers http://purl.org/coar/resource_type/c_6501