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Article Dans Une Revue Chemistry - A European Journal Année : 2018

Preparation of pillar[5]arene-based [2]rotaxanes by a stopper-exchange strategy

Résumé

A pillar[5]arene-containing rotaxane building block bearing exchangeable stoppers has been prepared in multigram scale quantities with high yields from the reaction of 2,4-dinitrophenol (DNP) with the inclusion complex resulting from the association of dodecanedioyl chloride with 1,4-diethoxypillar[5]arene. Stopper exchange reactions have been achieved by treatment of the resulting DNP diester with various amines through an addition–elimination mechanism preventing the unthreading of the axle component during the reaction and thus preserving the [2]rotaxane structures. The resulting diamide [2]rotaxane derivatives have thus been obtained in good to excellent yields. Importantly, [2]rotaxanes difficult or impossible to prepare by direct introduction of the two stoppers in a single synthetic step are now easily available.
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Dates et versions

hal-01957971 , version 1 (17-12-2018)

Identifiants

Citer

I. Nierengarten, Eric Meichsner, Michel Holler, Pauline Pieper, R. Deschenaux, et al.. Preparation of pillar[5]arene-based [2]rotaxanes by a stopper-exchange strategy. Chemistry - A European Journal, 2018, 24 (1), pp.169-177. ⟨10.1002/chem.201703997⟩. ⟨hal-01957971⟩
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