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Study of syn and anti Xenon-Cryptophanes Complexes Decorated with Aromatic Amine Groups: Chemical Platforms for Accessing New Cryptophanes

Martin Doll 1 Patrick Berthault 2 Estelle Léonce 2 Céline Boutin 2 Erwann Jeanneau 3 Thierry Brotin 1 Nicolas de Rycke 1 
2 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 : We report the synthesis of C3-symmetric cryptophanes decorated with three aromatic amine groups on the same CTB cap and their interaction with xenon. The relative stereochemistry of these two stereoisomers syn and anti was assessed thanks to the determination of the X-ray structure of an intermediate compound. As previously observed with the tris-aza-cryptophanes analogs anti-1 and syn-2 (J. Org. Chem. 2021, 86, 11, 7648–7658), both compounds anti-5 and syn-6 show a slow in–out exchange dynamics of xenon at 11.7 T. Our work supports the idea that the presence of nitrogen atoms grafted directly onto the cryptophane backbone has a strong impact on the in–out exchange dynamics of xenon whatever their stereochemistry. This result contrasts with the case of other cryptophanes decorated solely with methoxy substituents. Finally, we demonstrate that these new derivatives can be used to design new anti/syn cryptophanes bearing suitable ligands in order to constitute potent 129Xe NMR-based sensors. An example is reported here with the synthesis of the tris-iodo derivatives anti-13 and syn-14 from compounds anti-5 and syn-6.
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https://hal-cea.archives-ouvertes.fr/cea-03548300
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Submitted on : Sunday, January 30, 2022 - 11:16:06 AM
Last modification on : Monday, March 7, 2022 - 1:08:44 PM

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Martin Doll, Patrick Berthault, Estelle Léonce, Céline Boutin, Erwann Jeanneau, et al.. Study of syn and anti Xenon-Cryptophanes Complexes Decorated with Aromatic Amine Groups: Chemical Platforms for Accessing New Cryptophanes. Journal of Organic Chemistry, American Chemical Society, 2022, 87 (5), pp.2912-2920. ⟨10.1021/acs.joc.1c02774⟩. ⟨cea-03548300⟩

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