Pentafluorophenyl Esters as Exchangeable Stoppers for the Construction of Photoactive [2]rotaxanes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2021

Pentafluorophenyl Esters as Exchangeable Stoppers for the Construction of Photoactive [2]rotaxanes

Résumé

Stable pillar[5]arene-containing [2]rotaxane building blocks with pentafluorophenyl ester stoppers have been efficiently prepared on a multi-gram scale. Reaction of these building blocks with various nucleophiles gave access to a wide range of [2]rotaxanes with amide, ester or thioester stoppers in good to excellent yields. The rotaxane structure is fully preserved during these chemical transformations. Actually, the addition-elimination mechanism at work during these transformations totally prevents the unthreading of the axle moiety of the mechanically interlocked system. The stopper exchange reactions were optimized both in solution and under mechanochemical solvent-free conditions. While amide formation is more efficient in solution, the solvent-free conditions are more powerful for the transesterification reactions. Starting from a fullerene-functionalized pillar[5]arene derivative, this new strategy gave easy access to a photoactive [2]rotaxane incorporating a C60 moiety and two Bodipy stoppers. Despite the absence of covalent connectivity between the Bodipy and the fullerene moieties in this photoactive molecular device, efficient through-space excited state interactions have been evidenced in this rotaxane.

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Autre
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Dates et versions

hal-03368967 , version 1 (07-10-2021)

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Marine Rémy, Iwona Nierengarten, Boram Park, Michel Holler, Uwe Hahn, et al.. Pentafluorophenyl Esters as Exchangeable Stoppers for the Construction of Photoactive [2]rotaxanes. Chemistry - A European Journal, 2021, 27 (33), pp.8492-8499. ⟨10.1002/chem.202100943⟩. ⟨hal-03368967⟩
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