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

doi:10.1021/jacs.1c02230

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 journal › Article › peer-review

19 Scopus citations

Abstract

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 language	English (US)
Journal	Journal of the American Chemical Society
DOIs	https://doi.org/10.1021/jacs.1c02230
State	Published - 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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https://repository.kaust.edu.sa/bitstream/10754/669028/1/jacs.1c02230.pdf

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title = "Chemically Induced Mismatch of Rings and Stations in [3]Rotaxanes",

abstract = "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.",

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

note = "KAUST Repository Item: Exported on 2021-05-03 Acknowledgements: This work was supported by the European Union{\textquoteright}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).",

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doi = "10.1021/jacs.1c02230",

language = "English (US)",

journal = "Journal of the American Chemical Society",

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T1 - Chemically Induced Mismatch of Rings and Stations in [3]Rotaxanes

AU - Curcio, Massimiliano

AU - Nicoli, Federico

AU - Paltrinieri, Erica

AU - Fois, Ettore

AU - Tabacchi, Gloria

AU - Cavallo, Luigi

AU - Silvi, Serena

AU - Baroncini, Massimo

AU - Credi, Alberto

N1 - 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).

PY - 2021/4/29

Y1 - 2021/4/29

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/669028

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DO - 10.1021/jacs.1c02230

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SN - 0002-7863

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

ER -

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

Abstract

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