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

Zanichelli, Valeria ; Dallacasagrande, Luca ; Arduini, Arturo ; Secchi, Andrea ; Ragazzon, Giulio ; Silvi, Serena ; Credi, Alberto (2018) Electrochemically Triggered Co-Conformational Switching in a [2]catenane Comprising a Non-Symmetric Calix[6]arene Wheel and a Two-Station Oriented Macrocycle. Molecules, 23 (5). ISSN 1420-3049
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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.

Abstract
Document type
Article
Creators
CreatorsAffiliationORCID
Zanichelli, ValeriaUniversità di Parma
Dallacasagrande, LucaUniversità di Parma
Arduini, ArturoUniversità di Parma
Secchi, AndreaUniversità di Parma0000-0003-4045-961X
Ragazzon, GiulioUniversità di Bologna
Silvi, SerenaUniversità di Bologna0000-0001-9273-4148
Credi, AlbertoUniversità di Bologna0000-0003-2546-9801
Keywords
bipyridinium; calix[6]arenes; catenanes; electrochemistry; molecular machines; synthesis; ring-closing metathesis; voltammetry
Subjects
ISSN
1420-3049
DOI
Deposit date
16 May 2018 13:23
Last modified
23 May 2019 09:11
Project name
LEAPS - Light effected autonomous molecular pumps: Towards active transporters and actuating materials
Funding program
EC - H2020
URI

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