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Article Dans Une Revue Helvetica Chimica Acta Année : 2018

A Fullerene-Substituted Pillar[5]arene for the Construction of a Photoactive Rotaxane

Résumé

Transformation of a methylene group of the pillar[5]arene scaffold into a ketone has been achieved by treatment with N-bromosuccinimide followed by hydrolysis of the bromide intermediate and oxidation of the resulting secondary benzylic alcohol with BaMnO4. Condensation of the resulting macrocycle including a ketone function with p-toluenesulfonyl hydrazide followed by reaction of the corresponding tosylhydrazone with C60 under modified Bamford–Stevens conditions gave a fulleropillar[5]arene derivative. This building block has been used to prepare a rotaxane. The resulting molecule combining the fullerene-functionalized macrocycle with an axle bearing a porphyrin stopper is a photoactive molecular device in which the porphyrin emission is efficiently quenched by the fullerene moiety.

Mots clés

CMM

Domaines

Chimie organique
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Dates et versions

hal-02160715 , version 1 (19-06-2019)

Identifiants

Citer

Éric Meichsner, Iwona Nierengarten, Michel Holler, M Chessé, Jean-François Nierengarten. A Fullerene-Substituted Pillar[5]arene for the Construction of a Photoactive Rotaxane. Helvetica Chimica Acta, 2018, 101 (6), ⟨10.1002/hlca.201800059⟩. ⟨hal-02160715⟩
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