Tuning the structure of 1,3,5-benzene tricarboxamide self-assemblies through stereochemistry

Xavier Caumes; Arianna Baldi; Geoffrey Gontard; Patrick Brocorens; Roberto Lazzaroni; Nicolas Vanthuyne; Claire Troufflard; Matthieu Raynal; Laurent Bouteiller

doi:10.1039/C6CC07325E

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Tuning the structure of 1,3,5-benzene tricarboxamide self-assemblies through stereochemistry†

Xavier Caumes,^a Arianna Baldi,^a Geoffrey Gontard,^a Patrick Brocorens,^b Roberto Lazzaroni,^b Nicolas Vanthuyne,^c Claire Troufflard,^a Matthieu Raynal

*^a and Laurent Bouteiller^a

Author affiliations

* Corresponding authors

^a Sorbonne Universités, UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, F-75005 Paris, France
E-mail: matthieu.raynal@upmc.fr

^b Service de Chimie des Matériaux Nouveaux, Université de Mons/Materia Nova, Place du Parc, 20, B-7000 Mons, Belgium

^c Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France

Abstract

A heterochiral 1,3,5-benzene tricarboxamide (BTA) monomer, derived from valine dodecyl ester, forms long rods in cyclohexane whilst its homochiral analogue assembles into dimers only at the same concentration. This highly original assembly behaviour is related to the destabilization of the dimeric structure containing the two heterochiral monomers as corroborated by a combined experimental and computational study.

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

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DOI: https://doi.org/10.1039/C6CC07325E
Article type: Communication
Submitted: 07 Sept. 2016
Accepted: 20 Okt. 2016
First published: 20 Okt. 2016

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Chem. Commun., 2016,52, 13369-13372

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Tuning the structure of 1,3,5-benzene tricarboxamide self-assemblies through stereochemistry

X. Caumes, A. Baldi, G. Gontard, P. Brocorens, R. Lazzaroni, N. Vanthuyne, C. Troufflard, M. Raynal and L. Bouteiller, Chem. Commun., 2016, 52, 13369 DOI: 10.1039/C6CC07325E

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Chemical Communications

Tuning the structure of 1,3,5-benzene tricarboxamide self-assemblies through stereochemistry†

Abstract

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Tuning the structure of 1,3,5-benzene tricarboxamide self-assemblies through stereochemistry

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