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Updated: Jul 18, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Benzene Tetraamide: A Covalent Supramolecular Dual Motif in Dynamic Covalent Polymer Networks
Huiyi Zhang1, Annemiek van Hertrooij1, Tobias Schnitzer1
1Institute for Complex Molecular Systems & Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering & Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB Eindhoven, The Netherlands.
Abstract:
In dynamic polyamide networks, 1,2,4,5-benzene tetraamide (B4A) units act simultaneously as a dynamic covalent cross-linker and as supramolecular stacking motif. This results in materials with a rubbery plateau modulus that is about 20 times higher than that of a corresponding reference network in which the supramolecular interaction is suppressed. In branched polyamides with the same B4A dynamic motif, hydrogen bonding and stacking lead to strong and reversible supramolecular networks, whereas a branched polyamide with the nonstacking reference linker is a viscous liquid under the same conditions. Wide-angle X-ray scattering and variable-temperature infrared experiments confirm that covalent cross-linking and stacking cooperatively contribute to the dynamics of the network. Stress relaxation in the reference network is dominated by a single mode related to the dynamic covalent chemistry, whereas relaxation in the B4A network has additional modes assigned to the stacking dynamics.
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