Issue 24, 2023

Dynamic covalent self-assembly and self-sorting processes in the formation of imine-based macrocycles and macrobicyclic cages

Abstract

Investigating the self-assembly and self-sorting behaviour of dynamic covalent organic architectures makes possible the parallel generation of multiple discrete products in a single one pot procedure. We here report the self-assembly of covalent organic macrocycles and macrobicyclic cages from dialdehyde and polyamine components via multiple [2 + 2] and [3 + 2] polyimine condensations. Furthermore, component self-sorting processes have been monitored within the dynamic covalent libraries formed by these macrocycles and macrobicyclic cages. The progressive assembly of the final structures involves intermediates which undergo component selection and self-correction to generate the final thermodynamic constituents. The homo-self-sorting observed seems to involve entropic factors, as the homoleptic species present a higher symmetry than the competing heteroleptic ones. This study not only emphasizes the importance of an adequate design of the components of complex self-sorting systems, but also verifies the conjecture that systems of higher complexity may generate simpler outputs through the operation of competitive self-sorting.

Graphical abstract: Dynamic covalent self-assembly and self-sorting processes in the formation of imine-based macrocycles and macrobicyclic cages

Supplementary files

Article information

Article type
Edge Article
Submitted
03 mar 2023
Accepted
25 máj 2023
First published
02 jún 2023
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., 2023,14, 6631-6642

Dynamic covalent self-assembly and self-sorting processes in the formation of imine-based macrocycles and macrobicyclic cages

Z. Yang, F. Esteve, C. Antheaume and J. Lehn, Chem. Sci., 2023, 14, 6631 DOI: 10.1039/D3SC01174G

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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