Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
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Published on: November 9, 2019
Natalie Lagesse1, Luca Pisciottani1, Maxime Douarre1
1Institut des Sciences Moléculaires, CNRS UMR 5255, University of Bordeaux, Talence, France.
Abstract:
The templated clipping of a ferrocene-grafted isophthalic acid derivative to encircle a hydrogen-bonding axle through the reaction with 1,4-bis(aminomethyl)benzene is described. The constituent electroactive macrocycle of the resultant [2]rotaxane is a homologue of the versatile benchmark tetraamide variant developed by Leigh and co-workers. The relative templating effect of different hydrogen-bonding motifs in rotaxane and pseudorotaxane generation is compared, with yields varying from 0 to 41%. The electrochemical properties and single crystal X-ray structure of a doubly ferrocene-decorated [2]rotaxane are further reported.
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