title: Supramolecular ribbons from amphiphilic trisamides self-assembly.
abstract: Two amphiphilic C(3)-symmetric OPE-based trisamides have been synthesized and their self-assembling features investigated in solution and on surface. Variable-temperature UV-vis experiments demonstrate the cooperative supramolecular polymerization of these trisamides that self-assemble by the operation of triple C═O···H-N H-bonding arrays between the amide functional groups and π-π stacking between the aromatic units. The helical organization of the aggregates has been demonstrated by circular dichroism at a concentration as low as 1 × 10(-4) M in acetonitrile. In the reported trisamides, the large hydrophobic aromatic core acts as a solvophobic module impeding the interaction between the polar TEG chains and the amide H-bonds. This strategy makes unnecessary the separation of the amide functional groups to the polar tri(ethylene glycol) chains by paraffinic fragments. Achiral trisamide 1 self-assembles into flat ribbon-like structures that experience an amplification of chirality by the addition of a small amount of chiral 2 that generates twisted stripes.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias Químicas, Ciudad Universitaria s/n, 28040 Madrid, Spain.
authors.forename: Fátima
authors.initials: F
authors.lastname: García
authors.forename: Julia
authors.initials: J
authors.lastname: Buendía
authors.forename: Luis
authors.initials: L
authors.lastname: Sánchez