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Pappas, Charalampos G.; Mandal, Pradeep K.; Liu, Bin; Kauffmann, Brice; Miao, Xiaoming; Komaromy, David; Hoffmann, Waldemar; Manz, Christian; Chang, Rayoon; Liu, Kai; Pagel, Kevin; Huc, Ivan; Otto, Sijbren (2020): Emergence of low-symmetry foldamers from single monomers. In: Nature Chemistry, Vol. 12, No. 12: pp. 1180-1186
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Abstract

The majority of discrete structures obtained by self-assembly possess high symmetry, and thus low complexity: all subunits relate to their neighbours in a similar manner. Now, the spontaneous formation of complex low-symmetry assemblies produced from a single building block has been demonstrated using a systems chemistry approach. The single building block oligomerizes to form specific homomeric cyclic macromolecules that adopt a folded conformation. 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.