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Successive translocation of the rings in a [3]rotaxane

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cphc.201501162_accepted.pdf (2.215Mb)
Date
17/06/2016
Author
Jagesar, Dhiredj C.
Wiering, Piet G.
Kay, Euan R.
Leigh, David A.
Brouwer, Albert M.
Keywords
Electrochemistry
IR spectroscopy
Molecular devices
Reduction
Rotaxanes
QD Chemistry
NDAS
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Abstract
A [2]rotaxane, a [3]rotaxane and the corresponding thread containing two succinamide (succ) binding stations and a central redox-active pyromellitimide (pmi) station were studied. Infrared spectroelectrochemical experiments revealed the translocation of the macrocycle between the succinamide station and the electrochemically reduced pmi station (radical anion and dianion). Remarkably, in the [3]rotaxane, the rings can be selectively translocated. One-electron reduction leads to the translocation of one of the two macrocycles from the succinamide to the pyromellitimide station, whereas activation of the shuttle through two-electron reduction results in the translocation of both macrocycles: the dianion, due to its higher electron density and hence greater hydrogen-bond accepting affinity, is hydrogen bonded to both macrocycles. Systems with such an on-command contraction are known as molecular muscles. The relative strengths of the binding between the macrocycle and the imide anions could be estimated from the hydrogen-bond-induced shifts in the C=O stretching frequencies of hydrogen-bond accepting amide groups of the macrocycle.
Citation
Jagesar , D C , Wiering , P G , Kay , E R , Leigh , D A & Brouwer , A M 2016 , ' Successive translocation of the rings in a [3]rotaxane ' , ChemPhysChem , vol. 17 , no. 12 , pp. 1902-1912 . https://doi.org/10.1002/cphc.201501162
Publication
ChemPhysChem
Status
Peer reviewed
DOI
https://doi.org/10.1002/cphc.201501162
ISSN
1439-7641
Type
Journal article
Rights
Copyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/cphc.201501162
Description
This research was financially supported by the Netherlands Organization for the Advancement of Research (NOW).
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/10548

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