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Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle.

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.

SUBMITTER: Lagesse N

PROVIDER: S-EPMC7356209 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle.

Lagesse Natalie N Pisciottani Luca L Douarre Maxime M Godard Pascale P Kauffmann Brice B Martí-Centelles Vicente V McClenaghan Nathan D ND

Beilstein journal of organic chemistry 20200630

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% ...[more]

PMID: 32704322

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