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- Title
Functionalization of Bambusurils by a Thiol–Ene Click Reaction and a Facile Method for the Preparation of Anion‐Free Bambus[6]urils.
- Authors
Azazna, Djamille; Lafosse, Marine; Rivollier, Julie; Wang, Jialan; Cheikh, Imen Ben; Heck, Marie‐Pierre; Meyer, Michel; Thuéry, Pierre; Dognon, Jean‐Pierre; Huber, Gaspard
- Abstract
Abstract: Sulfide‐functionalized bambus[4]urils ((RS)8BU[4]) and bambus[6]urils ((RS)12BU[6]) were synthesized through thiol–ene click coupling reactions (TEC) of allylbambus[n]urils. Thiosugars were grafted to BU[4] and BU[6]. 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 allyl12BU[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 AgSbF6 to prepare anion‐free BU[6]. NMR spectroscopic methods were used to estimate association constants of these new empty BU[6] with different anions. Quantum chemical calculations were employed to rationalize the observed results. These new functionalized bambusuril scaffolds in alternate conformations could find applications as multivalent binders.
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 42, p10793
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201801468