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Helicity Inversion of Supramolecular Hydrogels Induced by Achiral Substituents
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
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2017 (English)In: ACS Nano, ISSN 1936-0851, E-ISSN 1936-086X, Vol. 11, no 12, p. 11880-11889Article in journal (Refereed) Published
Abstract [en]

Probing the supramolecular chirality of assemblies and controlling their handedness are closely related to the origin of chirality at the supramolecular level and the development of smart materials with desired handedness. However, it remains unclear how achiral residues covalently bonded to chiral amino acids can function in the chirality inversion of supramolecular assemblies. Herein, we report macroscopic chirality and dynamic manipulation of chiroptical activity of hydrogels self-assembled from phenylalanine derivatives, together with the inversion of their handedness achieved solely by exchanging achiral substituents between oligo(ethylene glycol) and carboxylic acid groups. This helicity inversion is mainly induced by distinct stacking mode of the self-assembled building blocks, as collectively confirmed by scanning electron microscopy, circular dichroism, crystallography, and molecular dynamics calculations. Through this straightforward approach, we were able to invert the handedness of helical assemblies by merely exchanging achiral substituents at the terminal of chiral gelators. This work not only presents a feasible strategy to achieve the handedness inversion of helical nanostructures for better understanding of chiral self-assembly process in supramolecular chemistry but also facilities the development of smart materials with controllable handedness in materials science.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2017. Vol. 11, no 12, p. 11880-11889
Keywords [en]
achiral substituent, helicity inversion, hydrogel, self-assembly, supramolecular chirality
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-221383DOI: 10.1021/acsnano.7b06097ISI: 000418990200013PubMedID: 29140680Scopus ID: 2-s2.0-85040033033OAI: oai:DiVA.org:kth-221383DiVA, id: diva2:1175101
Note

QC 20180117

Available from: 2018-01-17 Created: 2018-01-17 Last updated: 2018-01-29Bibliographically approved

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