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- Title
Synthesis and Characterisation of a Paramagnetic [2]Rotaxane Based on a Crown Ether‐Like Wheel Incorporating a Nitroxide Motif.
- Authors
Bleve, Valentina; Franchi, Paola; Konstanteli, Evangelia; Gualandi, Lorenzo; Goldup, Stephen M.; Mezzina, Elisabetta; Lucarini, Marco
- Abstract
Abstract: The synthesis of the new nitroxide crown ether <bold>8</bold> and its use as the wheel in a bistable [2]rotaxane, containing dialkylammonium and 4,4′‐bipyridinium recognition sites, is reported. The synthesis of <bold>8</bold> was achieved by the sequential addition of substituted phenyl groups to a nitrone derivatives leading to the preferential formation of the <italic>cis</italic> stereoisomer. Due to charge–dipole interactions between the nitroxide unit and the bipyridinium moiety, it was possible to probe the movement of the macrocycle between the two molecular stations of the [2]rotaxane after addition of a base by measuring the nitrogen hyperfine splitting in the corresponding EPR spectra. The equilibrium constant for the complexation of dibenzyl viologen by the macrocycle <bold>8</bold> was also determined by EPR titration.
- Subjects
NITROXIDE derivatives; NITRONE derivatives; SUBSTITUTION reactions; PHENYL group; STEREOISOMERS
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 5, p1198
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201704969