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7890260 
Journal Article 
A Fullerene-Substituted Pillar[5]arene for the Construction of a Photoactive Rotaxane 
Meichsner, E; Nierengarten, I; Holler, M; Chesse, M; Nierengarten, JF 
2018 
Yes 
Helvetica Chimica Acta
ISSN: 0018-019X 
Wiley Blackwell 
101 
6 
English 
WOS:000435272400004 
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. © 2018 Wiley-VHCA AG, Zurich, Switzerland 
Fullerenes; porphyrins; pillar[5]arenes; rotaxanes; photoactive molecular device