Discrepancy Regarding the Dethreading of a Dibenzo‐24‐crown‐8 Macrocycle through a Perfluorobutyl End in [2]Pseudorotaxanes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

Discrepancy Regarding the Dethreading of a Dibenzo‐24‐crown‐8 Macrocycle through a Perfluorobutyl End in [2]Pseudorotaxanes

Résumé

Here are reported the synthesis and characterization of four new dibenzo-24-crown-8 (DB24C8)-based ammonium-containing pseudorotaxanes, for which one of the two encircled axle's extremities consists of a perfluorobutyl moiety. The subsequent dethreading of the DB24C8 over the perfluorobutyl extremity was studied. Although the perfluorobutyl extremity of an ammonium-containing axle did not allow threading of DB24C8, dethreading of a perfluorobutyl extremity-containing pseudorotaxane was possible and its rate depended on both the strength of the template-to-DB24C8 complex and the nature of the axle. In particular, dethreading process may be assisted by the presence, in the threaded axle, of a poor secondary site of interaction for the DB24C8 and this assistance proved to be higher when this site is close to the DB24C8.

Domaines

Chimie organique
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Dates et versions

hal-04117927 , version 1 (25-06-2024)

Identifiants

Citer

Maxime Gauthier, Frédéric Coutrot. Discrepancy Regarding the Dethreading of a Dibenzo‐24‐crown‐8 Macrocycle through a Perfluorobutyl End in [2]Pseudorotaxanes. European Journal of Organic Chemistry, 2022, 2022 (21), pp.e202101201. ⟨10.1002/ejoc.202101201⟩. ⟨hal-04117927⟩
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