Chemically Induced Mismatch of Rings and Stations in [3]Rotaxanes

Massimiliano Curcio, Federico Nicoli, Erica Paltrinieri, Ettore Fois, Gloria Tabacchi, Luigi Cavallo, Serena Silvi, Massimo Baroncini, Alberto Credi

Research output: Contribution to journalArticlepeer-review

16 Scopus citations


The mechanical interlocking of molecular components can lead to the appearance of novel and unconventional properties and processes, with potential relevance for applications in nanoscience, sensing, catalysis, and materials science. We describe a [3]rotaxane in which the number of recognition sites available on the axle component can be changed by acid-base inputs, encompassing cases in which this number is larger, equal to, or smaller than the number of interlocked macrocycles. These species exhibit very different properties and give rise to a unique network of acid-base reactions that leads to a fine pKa tuning of chemically equivalent acidic sites. The rotaxane where only one station is available for two rings exhibits a rich coconformational dynamics, unveiled by an integrated experimental and computational approach. In this compound, the two crown ethers compete for the sole recognition site, but can also come together to share it, driven by the need to minimize free energy without evident inter-ring interactions.
Original languageEnglish (US)
JournalJournal of the American Chemical Society
StatePublished - Apr 29 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-05-03
Acknowledgements: This work was supported by the European Union’s H2020 Research and Innovation Program (ERC Advanced Grant n.692981), the Italian Ministry of University and Research (FARE R16S9XXKX3 and PRIN 20173L7W8K), and FAR2019 Uninsubria, and L.C. and E.F. acknowledge the
King Abdullah University of Science and Technology (KAUST) and the KAUST Supercomputing Laboratory (KSL) for support and for providing computational resources on the Shaheen II HPC system (project K1438).

ASJC Scopus subject areas

  • Biochemistry
  • Colloid and Surface Chemistry
  • General Chemistry
  • Catalysis


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