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Article Dans Une Revue Langmuir Année : 2012

Conformational Control of Hydrogen‐Bonded Aromatic Bis‐Ureas

Résumé

he phenylurea moiety is a ubiquitous synthon in supramolecular chemistry because it contains strong complementary hydrogen bonding groups and is synthetically very accessible. Here we investigate the possibility to strengthen self-association by conformational preorganization of the phenylurea moiety. In fact, we show that it is possible to strongly enhance intermolecular interactions between hydrogen bonded aromatic bis-ureas by substitution at the ortho positions of the phenylurea groups. Ortho substituents enforce a non-coplanar conformation of the urea and phenyl moieties better suited for hydrogen bonding. Substitution by methyl groups is more efficient than with larger groups, probably because of reduced steric hindrance. These effects have been demonstrated in the case of two different supramolecular architectures, which points to the probable generality of the phenomenon. In addition, this study has lead to the discovery of a new bis-urea able to form very stable self-assembled nanotubes in toluene up to high temperatures (boiling point) or low concentrations (10-7M) and in chloroform down to 3x10-4M.

Domaines

Chimie
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Dates et versions

hal-01696698 , version 1 (26-08-2020)

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Benjamin Isare, Gaëlle Pembouong, François Boué, Laurent Bouteiller. Conformational Control of Hydrogen‐Bonded Aromatic Bis‐Ureas. Langmuir, 2012, 28 (19), pp.7535--7541. ⟨10.1021/la300887p⟩. ⟨hal-01696698⟩
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