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Issue 44, 2019
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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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Supplementary files

Article information


Submitted
30 Jul 2019
Accepted
28 Sep 2019
First published
04 Oct 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 10422-10427
Article type
Edge Article

Programming permanent and transient molecular protection via mechanical stoppering

M. A. Soto, F. Lelj and M. J. MacLachlan, Chem. Sci., 2019, 10, 10422
DOI: 10.1039/C9SC03744F

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    [Original citation] - Published by The Royal Society of Chemistry.

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