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

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...

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Autores principales: Lagesse, Natalie, Pisciottani, Luca, Douarre, Maxime, Godard, Pascale, Kauffmann, Brice, Martí-Centelles, Vicente, McClenaghan, Nathan D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7356209/
https://www.ncbi.nlm.nih.gov/pubmed/32704322
http://dx.doi.org/10.3762/bjoc.16.128
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author Lagesse, Natalie
Pisciottani, Luca
Douarre, Maxime
Godard, Pascale
Kauffmann, Brice
Martí-Centelles, Vicente
McClenaghan, Nathan D
author_facet Lagesse, Natalie
Pisciottani, Luca
Douarre, Maxime
Godard, Pascale
Kauffmann, Brice
Martí-Centelles, Vicente
McClenaghan, Nathan D
author_sort Lagesse, Natalie
collection PubMed
description 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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spelling pubmed-73562092020-07-22 Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle Lagesse, Natalie Pisciottani, Luca Douarre, Maxime Godard, Pascale Kauffmann, Brice Martí-Centelles, Vicente McClenaghan, Nathan D Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2020-06-30 /pmc/articles/PMC7356209/ /pubmed/32704322 http://dx.doi.org/10.3762/bjoc.16.128 Text en Copyright © 2020, Lagesse et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Lagesse, Natalie
Pisciottani, Luca
Douarre, Maxime
Godard, Pascale
Kauffmann, Brice
Martí-Centelles, Vicente
McClenaghan, Nathan D
Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
title Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
title_full Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
title_fullStr Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
title_full_unstemmed Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
title_short Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
title_sort five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7356209/
https://www.ncbi.nlm.nih.gov/pubmed/32704322
http://dx.doi.org/10.3762/bjoc.16.128
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