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| Content Provider | Directory of Open Access Journals (DOAJ) |
|---|---|
| Author | Valeria Zanichelli Luca Dallacasagrande Arturo Arduini Andrea Secchi Giulio Ragazzon Serena Silvi Alberto Credi |
| 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. |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules23051156 |
| Journal | Molecules |
| Issue Number | 5 |
| Volume Number | 23 |
| Language | English |
| Publisher | MDPI AG |
| Publisher Date | 2018-05-01 |
| Publisher Place | Switzerland |
| Access Restriction | Open |
| Subject Keyword | Organic Chemistry Bipyridinium Calix[6]arenes Catenanes Electrochemistry Molecular Machines Synthesis Ring-closing Metathesis Voltammetry |
| Content Type | Text |
| Resource Type | Article |
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