Synthesis of Cryptophane-223-Type Derivatives with Dual Functionalization

Orsola Baydoun (1) , Nicolas de Rycke (1) , Estelle Léonce (2) , Céline Boutin (2) , Patrick Berthault (2) , Erwann Jeanneau (3) , Thierry Brotin (1)

1 LC - Laboratoire de Chimie - UMR5182
2 LSDRM - Laboratoire Structure et Dynamique par Résonance Magnétique (LCF)
3 UCBL - Université Claude Bernard Lyon 1

In this article, we present the synthesis of new cryptophane-type hosts capable of binding xenon in aqueous media and that may be useful for the development of xenon-based magnetic resonance imaging derivatives. The synthetic route proposed was chosen to facilitate both the introduction of water-solubilizing substituents and the functionalization of the host with a single arm showing recognition properties that constitute two crucial steps. This was made possible by preparing new cryptophane-223 derivatives bearing two different chemical functions that can be easily modified at a later stage. Thus, subsequent reactions allowed the design of a new cryptophane host able to bind zinc or nickel cations. The ability of this molecule to bind cationic species was assessed by calorimetric titration experiments and hyperpolarized 129Xe NMR. The advantages and disadvantages of this approach are discussed.

Domains: Chemical Sciences; Material chemistry

Orsola Baydoun, Nicolas de Rycke, Estelle Léonce, Céline Boutin, Patrick Berthault, et al.. Synthesis of Cryptophane-223-Type Derivatives with Dual Functionalization. Journal of Organic Chemistry, 2019, 84, pp.9127-9137. ⟨10.1021/acs.joc.9b01093⟩. ⟨cea-02183121⟩