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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.

SUBMITTER: Soto MA 

PROVIDER: S-EPMC6988755 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Programming permanent and transient molecular protection <i>via</i> mechanical stoppering.

Soto Miguel A MA   Lelj Francesco F   MacLachlan Mark J MJ  

Chemical science 20191004 44


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 c  ...[more]

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