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Aza-capped cyclodextrins for intra-cavity metal complexation

Abstract : Aza-capped, methylated cyclodextrins (CDs) were obtained in high yields by reacting the soft nitrogen nucleophile 2-nitrobenzenesulfonamide with either A, B-dimesylated CDs in basic media or their diol analogues under Mitsunobu reaction conditions followed by deprotection with thiophenol. A methyl pyridine substituent was grafted on the N atom of these secondary amines. When built on an alpha-CD scaffold, the resulting tertiary amine no longer undergoes nitrogen inversion at room temperature and behaves as a confining ligand, opening the way to intra-cavity metal complexation and promoting the formation of supramolecular helices.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01631752
Contributor : Laurent Jonchère <>
Submitted on : Thursday, November 9, 2017 - 4:27:27 PM
Last modification on : Monday, March 2, 2020 - 4:00:26 PM

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D. Sechet, Z. Kaya, T. -A. Phan, M. Jouffroy, E. Bentouhami, et al.. Aza-capped cyclodextrins for intra-cavity metal complexation. Chemical Communications, Royal Society of Chemistry, 2017, 53 (85), pp.11717-11720. ⟨10.1039/c7cc06434a⟩. ⟨hal-01631752⟩

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