Skip to content

Research at St Andrews

Successive translocation of the rings in a [3]rotaxane

Research output: Contribution to journalArticle

Author(s)

Dhiredj C. Jagesar, Piet G. Wiering, Euan R. Kay, David A. Leigh, Albert M. Brouwer

School/Research organisations

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.
Close

Details

Original languageEnglish
Pages (from-to)1902-1912
Number of pages11
JournalChemPhysChem
Volume17
Issue number12
Early online date29 Mar 2016
DOIs
Publication statusPublished - 17 Jun 2016

    Research areas

  • Electrochemistry, IR spectroscopy, Molecular devices, Reduction, Rotaxanes

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Programmable dynamic covalent nanoparticle building blocks with complementary reactivity

    Marro, N., della Sala, F. & Kay, E. R., 14 Nov 2019, In : Chemical Science. Advance Article

    Research output: Contribution to journalArticle

  2. Probing the interaction of nanoparticles with small molecules in real time via quartz crystal microbalance monitoring

    Yang, Y., Poss, G., Weng, Y., Qi, R., Zheng, H., Nianias, N., Kay, E. R. & Guldin, S., 21 Jun 2019, In : Nanoscale. 11, 23, p. 11107-11113 7 p.

    Research output: Contribution to journalArticle

  3. Twin-FRET: A New Molecular Ruler for Biomolecules

    Jana, S., Diez-Castellnou, M., Kay, E. R. & Penedo, C., 15 Feb 2019, In : Biophysical Journal. 116, 3, p. 565A-565A 1 p.

    Research output: Contribution to journalAbstract

  4. Optical trapping of ultrasmooth gold nanoparticles in liquid and air

    Arita, Y., Tkachenko, G., McReynolds, N., Marro, N., Edwards, W., Kay, E. R. & Dholakia, K., 25 Jun 2018, In : APL Photonics. 3, 8 p., 070801.

    Research output: Contribution to journalArticle

  5. Switchable selectivity within a series of boronate esters for dynamic covalent exchange in nonaqueous solvents

    Borsley, S., Poss, G., Spicer, R. L., Boudin, E. & Kay, E. R., 22 Feb 2018, In : Supramolecular Chemistry. Latest Articles, 10 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Monitoring complex formation by relaxation-induced pulse electron paramagnetic resonance distance measurements

    Giannoulis, A., Oranges, M. & Bode, B. E., 6 Sep 2017, In : ChemPhysChem. 18, 17, p. 2318-2321 5 p.

    Research output: Contribution to journalArticle

  2. N-heterocyclic carbene self-assembled monolayers on copper and gold: dramatic effect of wingtip groups on binding, orientation and assembly

    Larrea, C. R., Baddeley, C. J., Narouz, M. R., Mosey, N. J., Horton, J. H. & Crudden, C. M., 15 Dec 2017, In : ChemPhysChem. 18, 24, p. 3536–3539

    Research output: Contribution to journalArticle

  3. Fabrication of a high-quality, porous, surface-confined covalent organic framework on a reactive metal surface

    Larrea, C. R. & Baddeley, C. J., 4 Apr 2016, In : ChemPhysChem. 17, 7, p. 971–975

    Research output: Contribution to journalArticle

  4. From double-four-ring germanosilicates to new zeolites: in silico investigation

    Trachta, M., Bludský, O., Čejka, J., Morris, R. E. & Nachtigall, P., 6 Oct 2014, In : ChemPhysChem. 15, 14, p. 2972-2976 5 p.

    Research output: Contribution to journalArticle

ID: 241609830

Top