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Synthesis and properties of a redox-switchable calix[6]arene-based molecular lasso

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Abstract

The synthesis and characterisation of calix[6]arene-based lasso-like molecular structures is described. These interwoven structures consist of an electrochemical responsive N,N′-dialkylviologen arm covalently anchored at the upper rim of a triphenylureido calix[6]arene-based wheel. Upon reduction of the viologen core, a hollow tridimensional macrocyclic structure can be generated. This process is reversible, and the original lasso-like structure can be regenerated by oxidizing the viologen arm to its original dicationic form. Electrochemical and EPR techniques investigated the ability of the system to perform threading/dethreading movements upon redox switching. The functionalisation of the arm ω-hydroxy ending with a bulky diphenylacetyl group converts the self-threaded structure in a blocked interwoven molecular compound belonging to the class of [1]rotaxanes. The ability to form dimeric structures in the shape of a [c2]daisy chain was also demonstrated, an unprecedented result for calixarene macrocycles.

Graphical abstract: Synthesis and properties of a redox-switchable calix[6]arene-based molecular lasso

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Article information


Submitted
18 Nov 2019
Accepted
28 Dec 2019
First published
30 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Synthesis and properties of a redox-switchable calix[6]arene-based molecular lasso

G. Orlandini, L. Casimiro, M. Bazzoni, B. Cogliati, A. Credi, M. Lucarini, S. Silvi, A. Arduini and A. Secchi, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01379B

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