Issue 44, 2019

Programming permanent and transient molecular protection via mechanical stoppering

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2019,10, 10422-10427

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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