Shape‐Assisted Self‐Assembly of Hexa‐Substituted Carpyridines into 1D Supramolecular Polymers

Author:

Gallego Lucía1ORCID,Woods Joseph F.1ORCID,Butti Rachele1ORCID,Szwedziak Piotr2ORCID,Vargas Jentzsch Andreas3ORCID,Rickhaus Michel14ORCID

Affiliation:

1. Department of Chemistry University of Zurich Winterthurerstrasse 190 8057 Zurich Switzerland

2. Centre for Microscopy and Image Analysis University of Zurich Winterthurerstrasse 190 8057 Zurich Switzerland

3. SAMS Research Group University of Strasbourg, Institut Charles Sadron CNRS Rue du Loess 23 67200 Strasbourg France

4. Department of Organic Chemistry University of Geneva 30 quai Ernest-Ansermet 1205 Geneva Switzerland

Abstract

AbstractThe extent of the influence that molecular curvature plays on the self‐assembly of supramolecular polymers remains an open question in the field. We began addressing this fundamental question with the introduction of “carpyridines”, which are saddle‐shaped monomers that can associate with one another through π–π interactions and in which the rotational and translational movements are restricted. The topography displayed by the monomers led, previously, to the assembly of highly ordered 2D materials even in the absence of strong directional interactions such as hydrogen bonding. Here, we introduce a simple strategy to gain control over the dimensionality of the formed structures yielding classical unidimensional polymers. These have been characterized using well‐established protocols allowing us to determine and confirm the self‐assembly mechanism of both fibers and sheets. The calculated interaction energies are significantly higher than expected for flexible self‐assembling units lacking classical “strong” non‐covalent interactions. The versatility of this supramolecular unit to assemble into either supramolecular fibers or 2D sheets with strong association energies highlights remarkably well the potential and importance of molecular shape for the design of supramolecular materials and the applications thereof.

Funder

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Publisher

Wiley

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