Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane

Sissel S Andersen, Afaf W Saad, Rikke Kristensen, Teis S Pedersen, Luke J O'Driscoll, Amar H Flood, Jan O Jeppesen

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The rate at which the macrocyclic cyclobis(paraquat-p-phenylene) ring of a bistable [2]rotaxane moves from a tetrathiafulvalene station to an oxyphenylene station upon oxidation of the tetrathiafulvalene station is found to be increased in the presence of added salts. Compared to the salt-free case, 0.1 M solutions of a series of tetraalkylammonium hexafluorophosphate salts (R4N·PF6, R = H, Me, Et or n-Bu) and of tetrabutylammonium perchlorate (n-Bu4N·ClO4) all afford an increased switching rate, which is largest in the case of n-Bu4N·ClO4 with smaller anions. Variation in the size of the ammonium cation has no significant effect. These results indicate that the addition of excess ions can be used as an accelerator to speed up shuttling processes in rotaxanes and catenanes based on the mobile cyclobis(paraquat-p-phenylene) ring, and that the choice of anion offers a convenient means of controlling the extent of this effect.

OriginalsprogEngelsk
TidsskriftOrganic & Biomolecular Chemistry
Vol/bind17
Udgave nummer9
Sider (fra-til)2432-2441
ISSN1477-0520
DOI
StatusUdgivet - 5. feb. 2019

Fingeraftryk

Rotaxanes
Paraquat
Salts
Kinetics
Anions
Catenanes
Ammonium Compounds
Particle accelerators
Cations
Ions
Oxidation
tetrathiafulvalene

Citer dette

Andersen, S. S., Saad, A. W., Kristensen, R., Pedersen, T. S., O'Driscoll, L. J., Flood, A. H., & Jeppesen, J. O. (2019). Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane. Organic & Biomolecular Chemistry, 17(9), 2432-2441. https://doi.org/10.1039/c9ob00085b
Andersen, Sissel S ; Saad, Afaf W ; Kristensen, Rikke ; Pedersen, Teis S ; O'Driscoll, Luke J ; Flood, Amar H ; Jeppesen, Jan O. / Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane. I: Organic & Biomolecular Chemistry. 2019 ; Bind 17, Nr. 9. s. 2432-2441.
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title = "Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane",
abstract = "The rate at which the macrocyclic cyclobis(paraquat-p-phenylene) ring of a bistable [2]rotaxane moves from a tetrathiafulvalene station to an oxyphenylene station upon oxidation of the tetrathiafulvalene station is found to be increased in the presence of added salts. Compared to the salt-free case, 0.1 M solutions of a series of tetraalkylammonium hexafluorophosphate salts (R4N·PF6, R = H, Me, Et or n-Bu) and of tetrabutylammonium perchlorate (n-Bu4N·ClO4) all afford an increased switching rate, which is largest in the case of n-Bu4N·ClO4 with smaller anions. Variation in the size of the ammonium cation has no significant effect. These results indicate that the addition of excess ions can be used as an accelerator to speed up shuttling processes in rotaxanes and catenanes based on the mobile cyclobis(paraquat-p-phenylene) ring, and that the choice of anion offers a convenient means of controlling the extent of this effect.",
author = "Andersen, {Sissel S} and Saad, {Afaf W} and Rikke Kristensen and Pedersen, {Teis S} and O'Driscoll, {Luke J} and Flood, {Amar H} and Jeppesen, {Jan O}",
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language = "English",
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Andersen, SS, Saad, AW, Kristensen, R, Pedersen, TS, O'Driscoll, LJ, Flood, AH & Jeppesen, JO 2019, 'Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane', Organic & Biomolecular Chemistry, bind 17, nr. 9, s. 2432-2441. https://doi.org/10.1039/c9ob00085b

Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane. / Andersen, Sissel S; Saad, Afaf W; Kristensen, Rikke; Pedersen, Teis S; O'Driscoll, Luke J; Flood, Amar H; Jeppesen, Jan O.

I: Organic & Biomolecular Chemistry, Bind 17, Nr. 9, 05.02.2019, s. 2432-2441.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane

AU - Andersen, Sissel S

AU - Saad, Afaf W

AU - Kristensen, Rikke

AU - Pedersen, Teis S

AU - O'Driscoll, Luke J

AU - Flood, Amar H

AU - Jeppesen, Jan O

PY - 2019/2/5

Y1 - 2019/2/5

N2 - The rate at which the macrocyclic cyclobis(paraquat-p-phenylene) ring of a bistable [2]rotaxane moves from a tetrathiafulvalene station to an oxyphenylene station upon oxidation of the tetrathiafulvalene station is found to be increased in the presence of added salts. Compared to the salt-free case, 0.1 M solutions of a series of tetraalkylammonium hexafluorophosphate salts (R4N·PF6, R = H, Me, Et or n-Bu) and of tetrabutylammonium perchlorate (n-Bu4N·ClO4) all afford an increased switching rate, which is largest in the case of n-Bu4N·ClO4 with smaller anions. Variation in the size of the ammonium cation has no significant effect. These results indicate that the addition of excess ions can be used as an accelerator to speed up shuttling processes in rotaxanes and catenanes based on the mobile cyclobis(paraquat-p-phenylene) ring, and that the choice of anion offers a convenient means of controlling the extent of this effect.

AB - The rate at which the macrocyclic cyclobis(paraquat-p-phenylene) ring of a bistable [2]rotaxane moves from a tetrathiafulvalene station to an oxyphenylene station upon oxidation of the tetrathiafulvalene station is found to be increased in the presence of added salts. Compared to the salt-free case, 0.1 M solutions of a series of tetraalkylammonium hexafluorophosphate salts (R4N·PF6, R = H, Me, Et or n-Bu) and of tetrabutylammonium perchlorate (n-Bu4N·ClO4) all afford an increased switching rate, which is largest in the case of n-Bu4N·ClO4 with smaller anions. Variation in the size of the ammonium cation has no significant effect. These results indicate that the addition of excess ions can be used as an accelerator to speed up shuttling processes in rotaxanes and catenanes based on the mobile cyclobis(paraquat-p-phenylene) ring, and that the choice of anion offers a convenient means of controlling the extent of this effect.

U2 - 10.1039/c9ob00085b

DO - 10.1039/c9ob00085b

M3 - Journal article

VL - 17

SP - 2432

EP - 2441

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 9

ER -

Andersen SS, Saad AW, Kristensen R, Pedersen TS, O'Driscoll LJ, Flood AH et al. Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane. Organic & Biomolecular Chemistry. 2019 feb 5;17(9):2432-2441. https://doi.org/10.1039/c9ob00085b