Chiral Truxene‐Based Self‐Assembled Cages: Triple Interlocking and Supramolecular Chirogenesis

Author:

Séjourné Simon1,Labrunie Antoine1,Dalinot Clément1,Canevet David1ORCID,Guechaichia Romain1,Bou Zeid Jennifer1,Benchohra Amina1ORCID,Cauchy Thomas1ORCID,Brosseau Arnaud1,Allain Magali1ORCID,Chamignon Cécile2,Viger‐Gravel Jasmine2ORCID,Pintacuda Guido2ORCID,Carré Vincent3ORCID,Aubriet Frédéric3ORCID,Vanthuyne Nicolas4ORCID,Sallé Marc1ORCID,Goeb Sébastien1ORCID

Affiliation:

1. Univ Angers CNRS, MOLTECH-ANJOU F-49000 Angers France

2. Centre de RMN à Très Hauts Champs Université de Lyon (UMR 5082 CNRS/Ecole Normale Supérieure/Université Claude Bernard Lyon 1) 69100 Villeurbanne France

3. Université de Lorraine LCP-A2MC F-57000 Metz France

4. Aix Marseille Université, CNRS FSCM, Chiropole F-13397 Marseille France

Abstract

AbstractIncorporating chiral elements in host–guest systems currently attracts much attention because of the major impact such structures may have in a wide range of applications, from pharmaceuticals to materials science and beyond. Moreover, the development of multi‐responsive and ‐functional systems is highly desirable since they offer numerous benefits. In this context, we describe herein the construction of a metal‐driven self‐assembled cage that associates a chiral truxene‐based ligand and a bis‐ruthenium complex. The maximum separation between both facing chiral units in the assembly is fixed by the intermetallic distance within the lateral bis‐ruthenium complex (8.4 Å). The resulting chiral cavity was shown to encapsulate polyaromatic guest molecules, but also to afford a chiral triply interlocked [2]catenane structure. The formation of the latter occurs at high concentration, while its disassembly could be achieved by the addition of a planar achiral molecule. Interestingly the planar achiral molecule exhibits induced circular dichroism signature when trapped within the chiral cavity, thus demonstrating the ability of the cage to induce supramolecular chirogenesis.

Funder

Agence Nationale de la Recherche

Universite Angers

Publisher

Wiley

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