Issue 38, 2022

Emerging properties from mechanical tethering within a post-synthetically functionalised catenane scaffold

Abstract

Maintaining close spatial proximity of functional moieties within molecular systems can result in fascinating emergent properties. Whilst much work has been done on covalent tethering of functional units for myriad applications, investigations into mechanically linked systems are relatively rare. Formation of the mechanical bond is usually the final step in the synthesis of interlocked molecules, placing limits on the throughput of functionalised architectures. Herein we present the synthesis of a bis-azide [2]catenane scaffold that can be post-synthetically modified using CuAAC ‘click’ chemistry. In this manner we have been able to access functionalised catenanes from a common precursor and study the properties of electrochemically active, emissive and photodimerisable units within the mechanically interlocked system in comparison to non-interlocked analogues. Our data demonstrates that the greater (co-)conformational flexibility that can be obtained with mechanically interlocked systems compared to traditional covalent tethers paves the way for developing new functional molecules with exciting properties.

Graphical abstract: Emerging properties from mechanical tethering within a post-synthetically functionalised catenane scaffold

Supplementary files

Article information

Article type
Edge Article
Submitted
22 Jūl. 2022
Accepted
06 Sept. 2022
First published
16 Sept. 2022
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., 2022,13, 11368-11375

Emerging properties from mechanical tethering within a post-synthetically functionalised catenane scaffold

N. Hoyas Pérez, P. S. Sherin, V. Posligua, J. L. Greenfield, M. J. Fuchter, K. E. Jelfs, M. K. Kuimova and J. E. M. Lewis, Chem. Sci., 2022, 13, 11368 DOI: 10.1039/D2SC04101D

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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