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Influence of axle length on the rate and mechanism of shuttling in rigid H-shaped [2]rotaxanes

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Abstract

A series of [2]rotaxane molecular shuttles was prepared containing a dibenzo[24]crown-8 (DB24C8) wheel and a rigid H-shaped axle with varying track lengths between recognition sites; from 7.4 to 20.3 Å as defined by 1–4 phenyl rings or a naphthyl group. The rate of shuttling was measured by variable temperature 1H NMR spectroscopy for neutral compounds and EXSY experiments for dicationic species. The rates were found to be independent of the length of the axle, except when the distance between the two recognition sites might be short enough (n = 1) to allow the crown ether to simultaneously interact with both recognition sites providing a short-cut mechanism which could lower the energy barrier. This notion is supported by DFT calculations and solid-state characterization of model compounds that mimic possible transition states.

Graphical abstract: Influence of axle length on the rate and mechanism of shuttling in rigid H-shaped [2]rotaxanes

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Publication details

The article was received on 25 Aug 2017, accepted on 22 Sep 2017 and first published on 25 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC03736H
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Influence of axle length on the rate and mechanism of shuttling in rigid H-shaped [2]rotaxanes

    G. Gholami, K. Zhu, G. Baggi, E. Schott, X. Zarate and S. J. Loeb, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03736H

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