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

Natalie Lagesse; Luca Pisciottani; Maxime Douarre; Pascale Godard; Brice Kauffmann; Vicente Martí-Centelles; Nathan D McClenaghan

doi:10.3762/bjoc.16.128

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

Beilstein J Org Chem. 2020 Jun 30:16:1564-1571. doi: 10.3762/bjoc.16.128. eCollection 2020.

Authors

Natalie Lagesse¹, Luca Pisciottani¹, Maxime Douarre¹, Pascale Godard¹, Brice Kauffmann², Vicente Martí-Centelles¹, Nathan D McClenaghan¹

Affiliations

¹ Institut des Sciences Moléculaires, CNRS UMR 5255, University of Bordeaux, Talence, France.
² Institut Européen de Chimie et Biologie, CNRS UMS 3033, INSERM US001, University of Bordeaux, Pessac, 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.

Keywords: ferrocene; macrocycle; rotaxane; single crystal X-ray structure; template.

Grants and funding

This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No. 796612. Equally, financial support from the Agence Nationale de la Recherche (project ANR-16-CE29-0011, PETIMIT), University of Bordeaux; CNRS and Ministère de la Recherche et de l’Enseignement Supérieur (L.P. and N.L.) is gratefully acknowledged.