Symmetric Diarylalkyne Ligands for Metal‐Organic Cages

  • Author: European Journal of Organic Chemistry
  • Published Date: 01 April 2021
  • Copyright: Wiley-VCH GmbH
thumbnail image: Symmetric Diarylalkyne Ligands for Metal‐Organic Cages

Related Societies

Metal–organic cages are versatile molecular containers for the storage of molecules in a variety of applications, from catalysis to sensing. They are self-assembled from metal cations and organic ligands. However, the synthesis of these ligands is often a challenging and time-consuming multi-step process.

Anna J. McConnell, University of Kiel, Germany, and colleagues have developed a synthetic procedure for the efficient preparation of bipyridine- and benzimidazole-based ligands in the form of symmetric di(hetero)arylalkynes from simple (hetero)aryl halide precursors in one step (bipyridine-based example pictured below). The procedure uses cheap, commonly used reagents in a Sonogashira-type cross-coupling reaction. The team used Pd(PPh3)4 as the catalyst, trimethylsilylacetylene as an acetylene source, tetrabutylammonium fluoride (TBAF) as a base, activator, and deprotection reagent, and tetrahydrofuran (THF) as the solvent.


A variety of ligands were synthesized in good yields and with short reaction times. They can be used for the self-assembly of Co4L6-type metal-organic cages. Using this simple one-pot procedure, such ligands can be prepared with reduced synthetic effort, which could facilitate cage discovery. The researchers propose this procedure could not only be used for the synthesis of heterocyclic ligands but also for a wider scope of symmetric diarylalkynes.



Article Views: 1742

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH