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Molecules 2018, 23(5), 1156; https://doi.org/10.3390/molecules23051156

Electrochemically Triggered Co-Conformational Switching in a [2]catenane Comprising a Non-Symmetric Calix[6]arene Wheel and a Two-Station Oriented Macrocycle

1
Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Università di Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy
2
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, 40126 Bologna, Italy
3
Dipartimento di Scienze Chimiche, Università di Padova, 35131 Padova, Italy
4
Center for Light Activated Nanostructures (CLAN), Università di Bologna and Consiglio Nazionale delle Ricerche, 40129 Bologna, Italy
5
Dipartimento di Scienze e Tecnologie Agro-alimentari, Università di Bologna, 40127 Bologna, Italy
6
Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, 40129 Bologna, Italy
*
Authors to whom correspondence should be addressed.
Received: 12 April 2018 / Revised: 7 May 2018 / Accepted: 8 May 2018 / Published: 11 May 2018
(This article belongs to the Special Issue Interlocked Molecules, Molecular Machines, Motors and Muscles)
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Abstract

Catenanes with desymmetrized ring components can undergo co-conformational rearrangements upon external stimulation and can form the basis for the development of molecular rotary motors. We describe the design, synthesis and properties of a [2]catenane consisting of a macrocycle—the ‘track’ ring—endowed with two distinct recognition sites (a bipyridinium and an ammonium) for a calix[6]arene—the ‘shuttle’ ring. By exploiting the ability of the calixarene to thread appropriate non-symmetric axles with directional selectivity, we assembled an oriented pseudorotaxane and converted it into the corresponding oriented catenane by intramolecular ring closing metathesis. Cyclic voltammetric experiments indicate that the calixarene wheel initially surrounds the bipyridinium site, moves away from it when it is reduced, and returns in the original position upon reoxidation. A comparison with appropriate model compounds shows that the presence of the ammonium station is necessary for the calixarene to leave the reduced bipyridinium site. View Full-Text
Keywords: bipyridinium; calix[6]arenes; catenanes; electrochemistry; molecular machines; synthesis; ring-closing metathesis; voltammetry bipyridinium; calix[6]arenes; catenanes; electrochemistry; molecular machines; synthesis; ring-closing metathesis; voltammetry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Zanichelli, V.; Dallacasagrande, L.; Arduini, A.; Secchi, A.; Ragazzon, G.; Silvi, S.; Credi, A. Electrochemically Triggered Co-Conformational Switching in a [2]catenane Comprising a Non-Symmetric Calix[6]arene Wheel and a Two-Station Oriented Macrocycle. Molecules 2018, 23, 1156.

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