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Issue 6, 2019
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Dynamic polyimine macrobicyclic cryptands – self-sorting with component selection

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Abstract

Self-assembling macrobicyclic cryptand-type organic cages display remarkable self-sorting behavior with efficient component selection. Making use of the dynamic covalent chemistry approach, eight different cages were synthesized by condensation of tris(2-aminopropyl)amine with structurally different dialdehydes. A series of self-sorting experiments were first carried out on simple dynamic covalent libraries. They reveal the influence of different structural features of the aldehyde components on the condensation with two triamine capping units. Subsequently, self-sorting experiments were performed on more complex systems involving several dialdehyde building blocks. Altogether, the results obtained describe the effect of the presence of a heteroatom, of electrostatic interactions, of delocalization and of the flexibility/stiffness of the propensity of a component to undergo formation of a macrobicyclic cage. In the presence of a catalytic amount of acid, the macrobicyclic structure undergoes dynamic component exchange.

Graphical abstract: Dynamic polyimine macrobicyclic cryptands – self-sorting with component selection

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Supplementary files

Article information


Submitted
16 Oct 2018
Accepted
06 Dec 2018
First published
12 Dec 2018

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, 1836-1843
Article type
Edge Article

Dynamic polyimine macrobicyclic cryptands – self-sorting with component selection

M. Kołodziejski, A. R. Stefankiewicz and J. Lehn, Chem. Sci., 2019, 10, 1836 DOI: 10.1039/C8SC04598D

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