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Seeded Polymerization through the Interplay of Folding and Aggregation of an Amino‐Acid‐based Diamide
Author(s) -
Ogi Soichiro,
Matsumoto Kentaro,
Yamaguchi Shigehiro
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712119
Subject(s) - supramolecular chemistry , polymerization , supramolecular polymers , chemistry , folding (dsp implementation) , moiety , pyrene , intramolecular force , hydrogen bond , polymer , polymer chemistry , molecule , organic chemistry , electrical engineering , engineering
Amino acid based diamides are widely used as a substructure in supramolecular polymers and are also key components of polypeptides that help to understand protein folding. The interplay of folding and aggregation of a diamide was 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. Thermodynamics 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.