TY - JOUR AU - Stefaniu, Cristina AU - Zaffalon, Pierre-Léonard AU - Carmine, Alessio AU - Verolet, Quentin AU - Fernandez, Samuel AU - Wesolowski, Tomasz A. AU - Brezesinski, Gerald AU - Zumbuehl, Andreas TI - Rigid Urea and Self-Healing Thiourea Ethanolamine Monolayers PY - 2015 JF - Langmuir JA - Langmuir SN - 0743-7463 VL - 31 IS - 4 SP - 1296 EP - 1302 L1 - http://pubs.acs.org/doi/pdf/10.1021/la5039987 L2 - http://pubs.acs.org/doi/full/10.1021/la5039987 L3 - http://pubs.acs.org/doi/abs/10.1021/la5039987 L4 - http://www.unige.ch/sciences/chifi/publis/pics/double/ref01458.png M3 - 10.1021/la5039987 UR - http://dx.doi.org/10.1021/la5039987 N2 - 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. ID - 1458 ER -