2026-06-30T14:20:30Zhttps://docta.ucm.es/rest/oai/request

oai:docta.ucm.es:20.500.14352/948452024-09-24T14:41:15Zcom_20.500.14352_14col_20.500.14352_15

Supramolecular Ribbons from Amphiphilic Trisamides Self-Assembly García Melo, Fátima Buendía, Julia Sánchez Martín, Luis 547 54 Acetonitrile Amides Aromatic compounds Dichroism Ethylene Ethylene glycol Functional groups Self assembly Stereochemistry Química orgánica (Química) 23 Química Two amphiphilic C3-symmetric OPE-based trisamides have been synthesized and their self-assembling features investigated in solution and on surface. Variabletemperature UV vis experiments demonstrate the cooperative supramolecular polymerization of these trisamides that selfassemble by the operation of triple CdO 333 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 Ministerio de Ciencia, Innovación y Universidades (España) Depto. de Química Orgánica Fac. de Ciencias Químicas TRUE pub 2024-01-23T15:51:35Z 2024-01-23T15:51:35Z 2011 journal article VoR https://hdl.handle.net/20.500.14352/94845 1520-6904 10.1021/jo201055t eng (CTQ2008- 00795 Fátima García, Julia Buendía, and Luis Sánchez The Journal of Organic Chemistry 2011 76 (15), 6271-6276 DOI: 10.1021/jo201055t restricted access application/pdf ACS