Fiche publication
Date publication
février 2019
Journal
Chemical science
Auteurs
Membres identifiés du Cancéropôle Est :
Pr LEHN Jean-Marie
Tous les auteurs :
Kołodziejski M, Stefankiewicz AR, Lehn JM
Lien Pubmed
Résumé
Self-assembling macrobicyclic cryptand-type organic cages display remarkable self-sorting behavior with efficient component selection. Making use of the dynamic covalent chemistry approach, eight different cages were synthesized by condensation of tris(2-aminopropyl)amine with structurally different dialdehydes. A series of self-sorting experiments were first carried out on simple dynamic covalent libraries. They reveal the influence of different structural features of the aldehyde components on the condensation with two triamine capping units. Subsequently, self-sorting experiments were performed on more complex systems involving several dialdehyde building blocks. Altogether, the results obtained describe the effect of the presence of a heteroatom, of electrostatic interactions, of delocalization and of the flexibility/stiffness of the propensity of a component to undergo formation of a macrobicyclic cage. In the presence of a catalytic amount of acid, the macrobicyclic structure undergoes dynamic component exchange.
Référence
Chem Sci. 2019 Feb 14;10(6):1836-1843
