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Synthesis of Cryptophane-223-Type Derivatives with Dual Functionalization.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Jul 19; Vol. 84 (14), pp. 9127-9137. Date of Electronic Publication: 2019 Jul 05. - Publication Year :
- 2019
-
Abstract
- 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 <superscript>129</superscript> Xe NMR. The advantages and disadvantages of this approach are discussed.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 14
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31246016
- Full Text :
- https://doi.org/10.1021/acs.joc.9b01093