Seeded Polymerization through the Interplay of Folding and Aggregation of an Amino-Acid-based Diamide

Papers published
S. Ogi, K. Matsumoto, and S. Yamaguchi, Angew. Chem. Int. Ed., Early View. DOI: 10.1002/anie.201712119
(Back cover https://doi.org/10.1002/anie.201800993)
  • Amino-acid-based diamides are widely used as a substructure in supramolecular polymers, and also represent key components of polypeptides that help to understand protein folding. Herein, we report that the interplay of folding and aggregation of a diamide can be used to achieve seed-initiated supramolecular polymerization. For that purpose, a pyrene-substituted diamide was synthesized, in which pyrene is used as a tracer to monitor the supramolecular polymerization. Thermodynamic and time-dependent studies revealed that the folding of the diamide moiety, via the formation of intramolecular hydrogen bonds, effectively prevents a spontaneous nucleation that leads to supramolecular polymerization. Under such out-of-equilibrium conditions, the addition of seeds successfully initiates the supramolecular polymerization. These results demonstrate the utility of such amino-acid-based diamides in programmable supramolecular polymerizations.

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