Functionalization of Bambusurils by a thiol-ene click reaction and a facile method for the preparation of anion-free Bambus[6]urils - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2018

Functionalization of Bambusurils by a thiol-ene click reaction and a facile method for the preparation of anion-free Bambus[6]urils

Résumé

New sulfide‐functionalized bambus[4]urils ((RS)$_8$BU[4]) and bambus[6]urils ((RS)$_{12}$BU[6]) have been synthesized through thiol‐ene click coupling reactions (TEC) of allylbambus[n]urils. Synthesis of BU[6] derivatives always requires the use of a template anion (iodide, chloride or bromide) which is enclosed in the cavity of BU[6]. We show that this anion influences the reactivity of bambus[6]urils. An encapsulated iodide makes allyl functions of allyl$_{12}$BU[6] less reactive towards TEC and hydrogenation reactions in comparison to the corresponding chloride or bromide inclusion complexes. This is critical for the chemical reactivity of BU[6] and even more to determine their anion‐binding properties. We report a new, facile and fast method using AgSbF$_6$ to prepare anion‐free BU[6]. NMR methods were used to estimate association constants of these new empty BU[6] with different anions. Quantum chemistry calculations were employed to rationalize the observed results. These new functionalized bambusuril scaffolds in alternate conformation could find applications as multivalent binders.
Fichier principal
Vignette du fichier
ChemEurJ_18p10793_HAL.pdf (1.37 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

cea-01790936 , version 1 (11-02-2022)

Identifiants

Citer

Marie-Pierre Heck, Djamille Azazna, Marine Lafosse, Jialan Wang, Julie Rivollier, et al.. Functionalization of Bambusurils by a thiol-ene click reaction and a facile method for the preparation of anion-free Bambus[6]urils. Chemistry - A European Journal, 2018, 24, pp.10793 -10801. ⟨10.1002/chem.201801468⟩. ⟨cea-01790936⟩
125 Consultations
95 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More