Greciano Raiskila, Elisa EmiliaSchwalb, Alfonso J.Sánchez Martín, Luis2024-06-252024-06-252024Greciano EE, Schwalb AJ, Sánchez L. Effect of chirality in the supramolecular polymerization of N-annulated perylenediimides: Cancelling pathway complexity. Chirality. 2024; 36(2):e23639. doi:10.1002/chir.23639.0899-00421520-636X10.1002/chir.23639https://hdl.handle.net/20.500.14352/1052272024 Acuerdo transformativo financiado por la CRUEHerein, the synthesis of two chiral NPBIs, (S)-1 and (R)-1, is reported andtheir self-assembling features investigated. The reported NPBIs form chiralsupramolecular polymers with a rich dichroic pattern by the π-stacking of thearomatic backbones and the formation of an array of H-bonds between theamide functional groups. Furthermore, the peripheral 3,4,5-trialkoxy benza-mide groups can form seven-membered pseudocycles by the intramolecularH-bonding interaction between the NH of the peripheral amides and one ofthe carbonyls of the imide units thus yielding a kinetically controlled self-assembly process. Unlike achiral NPBI 1, that has been reported to form up tofour supramolecular polymorphs, the reported chiral NPBIs form only a J-typeaggregated species. The results presented herein reveal how subtle changesexert an enormous influence on the supramolecular polymerization outcomeengAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/journal articlehttps://doi.org/10.1002/chir.23639https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23639open access547Chiral supramolecular polymersJ-aggregatesPathway complexityPolymersSelf-assemblyQuímica orgánica (Química)2306 Química Orgánica