A Semiflexible Tetrahydrazone Macrocycle for Binding of Pyrophosphate and Smaller Anions

Lau Halgreen, Aaron Torres-Huerta, Karolis Norvaisa, Gaël De Leener, Nikolay Tumanov, Johan Wouters, Kristin Bartik, Hennie Valkenier

Résultats de recherche: Contribution à un journal/une revueArticleRevue par des pairs

Résumé

Macrocyclization has proven to be a useful design strategy in the development of efficient anion receptors. In addition to the ring size, the overall preorganization due to structural rigidity is key. To explore this in the context of developing an efficient pyrophosphate receptor, three macrocycles featuring a 26-membered interior ring size and similar H-bonding motifs have been synthesized, and their anion binding ability has been investigated. Computational studies and nuclear magnetic resonance (NMR) data showed different degrees of preorganization as a result of differences in flexibility. The interaction of the three macrocycles with chloride, dihydrogen phosphate, and dihydrogen pyrophosphate was investigated in solution by NMR and ultraviolet-visible spectroscopy and in the solid state by X-ray crystallography. The tetrahydrazone-based macrocycle featuring intermediate flexibility exhibited the best affinity for all three anions investigated. Our results suggest that in addition to the proper preorganization of binding groups in a macrocycle a certain degree of flexibility is also required for an optimal affinity with the target guest.

langue originaleAnglais
Pages (de - à)6853-6864
Nombre de pages12
journalJournal of Organic Chemistry
Volume89
Numéro de publication10
Les DOIs
Etat de la publicationPublié - 17 mai 2024

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