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A Fullerene‐Substituted Pillar[5]arene for the Construction of a Photoactive Rotaxane
Author(s) -
Meichsner Eric,
Nierengarten Iwona,
Holler Michel,
Chessé Matthieu,
Nierengarten JeanFrançois
Publication year - 2018
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201800059
Subject(s) - chemistry , rotaxane , porphyrin , moiety , fullerene , ketone , cycloaddition , photochemistry , molecule , polymer chemistry , metallacycle , supramolecular chemistry , organic chemistry , catalysis , x ray crystallography , physics , diffraction , optics
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 BaMnO 4 . Condensation of the resulting macrocycle including a ketone function with p ‐toluenesulfonyl hydrazide followed by reaction of the corresponding tosylhydrazone with C 60 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.