Chirality in Dynamic Supramolecular Nanotubes Induced by a Chiral Solvent

Benjamin Isare (1) , Mathieu Linares (2, 3) , Loussiné Zargarian (4) , Serge Fermandjian (4) , Motofumi Miura (5) , Shigeyasu Motohashi (5) , Nicolas Vanthuyne (6) , Roberto Lazzaroni (2) , Laurent Bouteiller (1)

1 LCP - Chimie des polymères
2 Service de Chimie des Matériaux Nouveaux, CIRMAP, University of Mons
3 Linköpings universitet
4 LBPA - Laboratoire de Biologie et de Pharmacologie Appliquée
5 Nihon University
6 CCB - Chirotechnologies : Catalyse et Biocatalyse

Amplification of chirality has been reported in polymeric systems. It has also been shown that related effects can occur in polymer‐like dynamic supramolecular aggregates, if a subtle balance between noncovalent interactions allows the coupling between a chiral information and a cooperative aggregation process. In this context, we report a strong majority‐rules effect in the formation of chiral dynamic nanotubes from chiral bisurea monomers. Furthermore, similar helical nanotubes (with the same circular dichroism signature) can be obtained from racemic monomers in a chiral solvent. Competition experiments reveal the relative strength of the helical bias induced by the chiral monomer or by the chiral solvent. The nanotube handedness is imposed by the monomer chirality, whatever the solvent chirality. However, the chirality of the solvent has a significant effect on the degree of chiral induction.

Mots clés: chirality; chiral solvent; nano-tubes; supramolecular chemistry; self- assembly

Domaines: Chimie

Benjamin Isare, Mathieu Linares, Loussiné Zargarian, Serge Fermandjian, Motofumi Miura, et al.. Chirality in Dynamic Supramolecular Nanotubes Induced by a Chiral Solvent. Chemistry - A European Journal, 2010, 16 (1), pp.173--177. ⟨10.1002/chem.200902399⟩. ⟨hal-01696713⟩