4.8 Review

Challenges and Opportunities in the Post-Synthetic Modification of Interlocked Molecules

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 31, Pages 16778-16799

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007496

Keywords

interlocked molecules; mechanical bonds; post-synthetic modification; rotaxanes; self-assembly

Funding

  1. Agence Nationale de la Recherche [ANR-17-CE07-0014-01]
  2. Agence Nationale de la Recherche (ANR) [ANR-17-CE07-0014] Funding Source: Agence Nationale de la Recherche (ANR)

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The synthesis of interlocked molecules often involves the challenging post-synthetic modifications while conserving the mechanical bond. To overcome synthetic problems, a strategy of synthesizing isolable and storable interlocked building blocks before modification is appealing. The reactivity of functional groups and preservation of the interlocked architecture are closely linked to the fundamental role of the mechanical bond in the strategy employed.
Several strategies have been successfully utilised to obtain a wide range of interlocked molecules. However, some interlocked compounds are still not obtained directly and/or efficiently from non-interlocked components because the requisites for self-assembly cannot always be enforced. To circumvent such a synthetic problem, a strategy that consists of synthesizing an isolable and storable interlocked building block in a step that precedes its modification is an appealing chemical route to more sophisticated interlocked molecules. Synthetic opportunities and challenges are closely linked to the fact that the mechanical bond might greatly affect the reactivity of a functionality of the encircled axle, but that the interlocked architecture needs to be preserved during the synthesis. Hence, the mechanical bond plays a fundamental role in the strategy employed. This Review focuses on the challenging post-synthetic modifications of interlocked molecules, sometimes through cleavage of the axle's main chain, but always with conservation of the mechanical bond.

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