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Synthesis 2009(9): 1506-1512  
DOI: 10.1055/s-0028-1088159
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Azido- and Ethynyl-Substituted 2,2′:6′,2′′-Terpyridines as Suitable Substrates for Click Reactions

Andreas Wintera, Andreas Wildb, Richard Hoogenbooma, Martin W. M. Fijtena, Martin D. Hagerb, Reza-Ali Fallahpourc, Ulrich S. Schubert*a,b
a Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands
Fax: +31(40)2474186; e-Mail: u.s.schubert@tue.nl;
b Laboratory of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
c HetCat, Gundeldingerstr. 174, 4053 Basel, Switzerland
Further Information

Publication History

Received 27 September 2008
Publication Date:
25 March 2009 (online)

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Abstract

The click reaction of azido- and ethynyl-functionalized terpyridines has been exploited to obtain a series of 1H-1,2,3-triazole-substituted terpyridines. This protocol was extended towards the synthesis of terpyridine-based macroligands via end group modification of ethynyl-functionalized polymers. Finally, the combination of two orthogonal terpyridines within one click reaction highlights the potential of this approach with respect to the preparation of new building blocks for supramolecular assemblies and functional materials.

Key words

click reaction - complexes - cycloaddition - ligands - terpyridines

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A detailed investigation of the electrooptical properties of 1H-1,2,3-triazole-containing terpyridine derivatives, supported by DFT calculations is currently ongoing will be published elewhere.