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Emergence of low-symmetry foldamers from single monomers

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Hoffmann,  Waldemar
Institute of Chemistry and Biochemistry, Freie Universität Berlin;
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Manz,  Christian
Institute of Chemistry and Biochemistry, Freie Universität Berlin;
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Chang,  Rayoon
Institute of Chemistry and Biochemistry, Freie Universität Berlin;
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Pagel,  Kevin
Institute of Chemistry and Biochemistry, Freie Universität Berlin;
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Citation

Pappas, C. G., Mandal, P. K., Liu, B., Kauffmann, B., Miao, X., Komáromy, D., et al. (2020). Emergence of low-symmetry foldamers from single monomers. Nature Chemistry, 12, 1180-1186. doi:10.1038/s41557-020-00565-2.


Cite as: http://hdl.handle.net/21.11116/0000-0007-75BD-1
Abstract
Self-assembly is a powerful method to obtain large discrete functional molecular architectures. When using a single building block, self-assembly generally yields symmetrical objects in which all the subunits relate similarly to their neighbours. Here we report the discovery of a family of self-constructing cyclic macromolecules with stable folded conformations of low symmetry, which include some with a prime number (13, 17 and 23) of units, despite being formed from a single component. The formation of these objects amounts to the production of polymers with a perfectly uniform length. Design rules for the spontaneous emergence of such macromolecules include endowing monomers with a strong potential for non-covalent interactions that remain frustrated in competing entropically favoured yet conformationally restrained smaller cycles. The process can also be templated by a guest molecule that itself has an asymmetrical structure, which paves the way to molecular imprinting techniques at the level of single polymer chains.