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Programming permanent and transient molecular protection via mechanical stoppering

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Abstract

Chemical protection is an essential tool in synthetic chemistry, which involves blocking reactive sites on a molecule through covalent bonds. Physical approaches, such as encapsulation and host-mediated protection, have emerged as interesting alternatives that use steric bulk to inhibit reactivity. Here, we report the protection of a redox-active viologen through its incorporation into mechanically interlocked molecules (MIMs), namely hetero[4]rotaxanes. The viologen was confined inside a host cavity and flanked by two mechanical stoppers, which allowed for permanent and transient protection. Deprotection occurred on-demand via an unstoppering process, triggered by a proton transfer, polarity effect, or a thermal stimulus. We anticipate that permanent and transient mechanical stoppering could be incorporated into devices to function as molecular probes, transport/delivery systems, or stimuli-controlled degradable materials.

Graphical abstract: Programming permanent and transient molecular protection via mechanical stoppering

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Publication details

The article was received on 30 Jul 2019, accepted on 28 Sep 2019 and first published on 04 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC03744F
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Programming permanent and transient molecular protection via mechanical stoppering

    M. A. Soto, F. Lelj and M. J. MacLachlan, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03744F

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