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

Pierre Heck 1 Djamille Azazna 1 Marine Lafosse 1 Jialan Wang 1 Julie Rivollier 1 Imen Ben Cheikh 1 Michel Meyer 1 Pierre Thuéry 2 Jean-Pierre Dognon 3 Gaspard Huber 3
1 SCBM - Service de Chimie Bio-Organique et de Marquage
2 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
3 LSDRM - Laboratoire Structure et Dynamique par Résonance Magnétique (LCF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
Abstract : New sulfide‐functionalized bambus[4]urils ((RS)8BU[4]) and bambus[6]urils ((RS)12BU[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 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 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.
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Journal articles
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https://hal-cea.archives-ouvertes.fr/cea-01790936
Contributor : Serge Palacin <>
Submitted on : Monday, May 14, 2018 - 10:54:28 AM
Last modification on : Thursday, March 7, 2019 - 3:34:14 PM

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CEA | DSM-IRAMIS | PUBNIMBE | IRAMIS-NIMBE | CEA-UPSAY | CEA-DRF | INC-CNRS | UNIV-PARIS-SACLAY | JOLIOT | DMTS

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Pierre Heck, Djamille Azazna, Marine Lafosse, Jialan Wang, Julie Rivollier, et al.. Functionalization of Bambusurils by thiol-ene click reaction and new, facile method for the preparation of anion-free Bambus[6]urils. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24, pp.10793 -10801. ⟨https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801468⟩. ⟨10.1002/chem.201801468⟩. ⟨cea-01790936⟩

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