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The Bis-urea Motif as a Tool To Functionalize Self-Assembled Nanoribbons

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journal contribution
posted on 07.12.2005, 00:00 authored by Matthijn R. J. Vos, Gorka Etxebarria Jardĺ, Anna Llanes Pallas, Monica Breurken, Otto L. J. van Asselen, Paul H. H. Bomans, Phillip E. L. G. Leclère, Peter M. Frederik, Roeland J. M. Nolte, Nico A. J. M. Sommerdijk
Here we present a surfactant molecule (1) containing an ammonium headgroup, in which a bis-ureido group is incorporated in its hydrocarbon chain. Due to strong hydrogen bonding interactions, 1 forms well-defined highly ordered ribbon-like aggregates in water. Moreover, we demonstrate that these ribbons can be functionalized via a modular approach through molecular recognition of other bis-urea containing molecules. The dye disperse orange and biotin were coupled to matching bis-ureido groups and incorporated into the ribbon structure. The anchoring of different functionalities in a modular approach proved to be possible using the molecular recognition capabilities of the bis-ureido moiety, thereby opening possibilities to a wide range of applications.