Issue 10, 2022

Fast, solvent-free synthesis of ferrocene-containing organic cages via dynamic covalent chemistry in the solid state

Abstract

A simple, solvent-free synthetic protocol towards the synthesis of organic self-assembled macromolecules has been established. By employing mechanochemistry using glassware readily available to every organic chemist, we were able to synthesise three novel organic cage compounds exemplarily and to speed up the synthesis of a ferrocene-containing macrocycle by a factor of 288 compared to the solution-based synthesis. The structural investigation of the newly synthesised cages revealed different modes of connectivity from using ferrocene-containing aldehydes caused by the free rotation of the cyclopentadienyl units against each other. By extending the facile solvent-free synthesis to ball-milling, even compounds that show lower reactivity could be employed in the dynamic covalent formation of organometallic cage compounds. The presented protocol gives access to otherwise inaccessible structures, speeds up general synthetic workflows, and simultaneously reduces the environmental impact of supramolecular syntheses.

Graphical abstract: Fast, solvent-free synthesis of ferrocene-containing organic cages via dynamic covalent chemistry in the solid state

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Nov 2021
Accepted
31 Jan 2022
First published
03 Feb 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-NC license

Chem. Sci., 2022,13, 2877-2883

Fast, solvent-free synthesis of ferrocene-containing organic cages via dynamic covalent chemistry in the solid state

T. Kunde, T. Pausch, P. A. Guńka, M. Krzyżanowski, A. Kasprzak and B. M. Schmidt, Chem. Sci., 2022, 13, 2877 DOI: 10.1039/D1SC06372C

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