Chiral functional assemblies

CONTRIBUTORS : Matthieu RAYNAL, Laurent BOUTEILLER

We are interested in the structure-property relationships of discrete chiral species or (co)polymers formed by hydrogen bonds, whether crystalline, in solution or in gel form. This includes experimental and MM/MD characterisation of unusual assemblies of BTA esters[1] or bis-ureas[2] and characterisation of helical catalysts[3]. The chemical nature of the group connected to the stereogenic centres of BTA esters has a major influence on the structure of the associated self-assemblies: in particular, various types of dimeric structures[4-6] or reinforced helical stacks[7] have been characterised. Of particular interest was the induction of a chiral environment in linear gold[8] and plano-square platinum[9] complexes located at the periphery of sergeant/soldier type assemblies. Finally, benzene-1-urea-3,5-bisamide (BUBA) monomers, composed of a urea function and two amide functions linked to an aromatic core, constitute an easily accessible class of C2-symmetric supramolecular synthons that exhibit a good sergeant/soldier effect[10].

Structures of assemblies formed by hydrogen bonds with their chiroptic signature.

Publications associées :

[1] Revisiting the assembly of amino ester-based benzene-1,3,5-tricarboxamides: chiral rods in solution

Alaric Desmarchelier,Matthieu Raynal,*Patrick Brocorens, Nicolas Vanthuyne, Laurent Bouteiller* Chem. Commun., 2015, 51, 7397-7400

[2] Structural control of bisurea-based supramolecular polymers: influence of an ester moiety

Mohammed Dirany, Virgile Ayzac, Benjamin Isare, Matthieu Raynal,* Laurent Bouteiller* Langmuir, 2015, 31, 11443-11451

[3] Dissecting the role of the sergeants in supramolecular helical catalysts: From chain capping to intercalation

Mayte A. Martínez-Aguirre, Yan Li, Nicolas Vanthuyne, Laurent Bouteiller, Matthieu Raynal* Angew. Chem. Int. Ed., 2021, 60, 4183-4191

[4] Tuning the nature and stability of self-assemblies formed by ester benzene 1,3,5-tricarboxamides: the crucial role played by the substituents

Alaric Desmarchelier, Bruno Giordano Alvarenga, Xavier Caumes, Ludovic Dubreucq, Claire Troufflard, Martine Tessier, Nicolas Vanthuyne, Julien Idé, Thomas Maistriaux, David Beljonne, Patrick Brocorens, Roberto Lazzaroni, Matthieu Raynal,* Laurent Bouteiller Soft Matter, 2016, 12, 7824-7838

[5] 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 Chem. Commun., 2016, 52, 13369-13372

[6] Experimental and computational diagnosis of the fluxional nature of a benzene-1,3,5-tricarboxamide-based hydrogen-bonded dimer

Matthieu Raynal,* Yan Li, Claire Troufflard, Cédric Przybylski, Geoffrey Gontard, Thomas Maistriaux, Julien Idé, Roberto Lazzaroni, Laurent Bouteiller, Patrick Brocorens* Phys. Chem. Chem. Phys., 2021, 23, 5207-5221

[7] Extra hydrogen bonding interactions by peripheral indole groups stabilize benzene-1,3,5-tricarboxamide helical assemblies

Gaëtan Basuyaux, Alaric Desmarchelier, Geoffrey Gontard, Nicolas Vanthuyne, Jamal Moussa,* Hani Amouri, Matthieu Raynal* Laurent Bouteiller Chem. Commun., 2019, 55, 8548-8551

[8] Induced circular dichroism in phosphine gold(I) arylacetylide urea complexes through hydrogen-bonded chiral co-assemblies

Julien Dubarle-Offner, Jamal Moussa, Hani Amouri,* Benjamin Jouvelet, Laurent Bouteiller, Matthieu Raynal* Chem. Eur. J., 2016, 22, 3985-3990

[9] Cyclometallated Pt(II) complexes containing a functionalized bis-urea alkynyl ligand: Probing aggregation mediated by hydrogen bonds versus Pt∙∙∙Pt and π-π interactions

G. Basuyaux, A. Amar, C. Troufflard, A. Boucekkine, R. Metivier, M. Raynal,* J. Moussa, L. Bouteiller, H. Amouri* Eur. J. Inorg. Chem., 2021, 35, 3622-3631

[10] N-Substituted benzene-1-urea-3,5-biscarboxamide (BUBA): Easily accessible C2-symmetric monomers for the construction of reversible and chirally amplified helical assemblies

Yan Li, Ludovic Dubreucq, Bruno G. Alvarenga, Matthieu Raynal,* Laurent Bouteiller Chem. Eur. J., 2019, 25, 10650-10661