Supramolecular Double Helices from Small C3-symmetrical Molecules Aggregated in Water

René P M Lafleur, Svenja Herziger, Sandra M C Schoenmakers, Arthur D A Keizer, Jahaziel Jahzerah, Bala N S Thota, Lu Su, Paul H H Bomans, Nico A J M Sommerdijk, Anja R A Palmans, Rainer Haag, Heiner Friedrich, Christoph Böttcher (Corresponding author), Egbert Willem Meijer (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Supramolecular fibers in water, micrometers long and several nanometers in width, are amongst the most studied nanostructures for biomedical applications. These supramolecular polymers are formed through a spontaneous self-assembly process of small amphiphilic molecules by specific secondary interactions. Although many compounds do not possess a stereocenter, recent studies suggest the (co-)existence of helical structures, albeit in racemic form. Here, we disclose a series of supramolecular (co)polymers based on water-soluble benzene-1,3,5-tricarboxamides (BTAs) that form double helices, fibers that for long were thought to be chains of single molecules stacked in one dimension (1D). Detailed cryo-TEM studies and subsequent 3D-volume reconstructions unveiled helical repeats, ranging from 15-30 nanometer. Most remarkable, the pitch can be tuned through the composition of the copolymers, where two different monomers with the same core but different peripheries are mixed in various ratios. Like in lipid bilayers, the hydrophobic shielding in the aggregates of these disc-shaped molecules is proposed to be best obtained by dimer-formation promoting supramolecular double helices. It is anticipated that many of the supramolecular polymers in water will have a thermodynamic stable structure being such a double helix, although small structural changes can yield single stacks as well. Hence, it is essential to perform detailed analyses prior to sketching a molecular picture of these 1D fibers.

Original languageEnglish
Pages (from-to)17644-17652
Number of pages9
JournalJournal of the American Chemical Society
Volume142
Issue number41
Early online date29 Sep 2020
DOIs
Publication statusPublished - 14 Oct 2020

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