Consequences of conformational flexibility in hydrogen-bond-driven self-assembly processes

José Augusto Berrocal; Florent Di Meo; Miguel García-Iglesias; Ronald P. J. Gosens; E. W. Meijer; Mathieu Linares; Anja R. A. Palmans

doi:10.1039/C6CC05593A

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Consequences of conformational flexibility in hydrogen-bond-driven self-assembly processes†

José Augusto Berrocal,‡^a Florent Di Meo,‡^bc Miguel García-Iglesias,‡^a Ronald P. J. Gosens,^a E. W. Meijer,^a Mathieu Linares*^bd and Anja R. A. Palmans*^a

Author affiliations

* Corresponding authors

^a Institute for Complex Molecular Systems, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands
E-mail: a.palmans@tue.nl

^b Department of Physics, Chemistry and Biology (IFM), Linköping University, SE-581 83 Linköping, Sweden
E-mail: mathieu@ifm.liu.se

^c INSERM UMR 850, Univ. Limoges, School of Pharmacy, 2 rue Dr Marcland, F-87025 Limoges, France

^d Swedish e-Science Research Centre (SeRC), Linköping University, SE-581 83 Linköping, Sweden

Abstract

We report the synthesis and self-assembly of chiral, conformationally flexible C₃-symmetrical trisamides. A strong Cotton effect is observed for the supramolecular polymers in linear alkanes but not in cyclic alkanes. MD simulations suggest 2 : 1 conformations of the amides within the aggregates in both types of solvents, but a chiral bias in only linear alkanes.

This article is part of the themed collection: Chirality at the nanoscale

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DOI: https://doi.org/10.1039/C6CC05593A
Article type: Communication
Submitted: 06 Jul 2016
Accepted: 01 Aug 2016
First published: 02 Aug 2016
This article is Open Access

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Chem. Commun., 2016,52, 10870-10873

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Consequences of conformational flexibility in hydrogen-bond-driven self-assembly processes

J. A. Berrocal, F. Di Meo, M. García-Iglesias, R. P. J. Gosens, E. W. Meijer, M. Linares and A. R. A. Palmans, Chem. Commun., 2016, 52, 10870 DOI: 10.1039/C6CC05593A

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Chemical Communications

Consequences of conformational flexibility in hydrogen-bond-driven self-assembly processes†

Abstract

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Consequences of conformational flexibility in hydrogen-bond-driven self-assembly processes

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