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Langmuir. 2015 Feb 3;31(4):1296-302. doi: 10.1021/la5039987. Epub 2015 Jan 16.

Rigid urea and self-healing thiourea ethanolamine monolayers.

Author information

1
Max Planck Institute of Colloids and Interfaces , 14476 Potsdam, Germany.

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.

PMID:
25594235
DOI:
10.1021/la5039987
[Indexed for MEDLINE]

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