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Issue 25, 2012
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Functionalisation of lanthanide complexes via microwave-enhanced Cu(I)-catalysed azide–alkyne cycloaddition

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Abstract

CuI-catalysed azide–alkyne cycloaddition reactions were used to functionalise lanthanideIII-complexes (Ln; La, Eu and Tb) incorporating alkyne or azide reactive groups. Microwave irradiation significantly accelerated the reactions, enabling full conversion to the triazole products in some cases in 5 min. Alkyl and aryl azides and alkyl and aryl alkynes could all serve as coupling partners. These reaction conditions proved efficient for cyclen-tricarboxylates and previously unreactive cyclen-tris-primary amide chelates. The synthesis of heterobimetallic (Eu/Tb, EuTb17 and Eu/La, EuLa17) and heterotrimetallic (Eu/La/Eu) complexes was achieved in up to 60% isolated yield starting from coumarin 2-appended alkynyl complexes Tb16 or La16 and an azido-Eu complex Eu4, and bis-alkynyl La-complex La5 and Eu4, respectively. EuTb17 displayed dual EuIII and TbIII-emission upon antenna-centred excitation.

Graphical abstract: Functionalisation of lanthanide complexes via microwave-enhanced Cu(i)-catalysed azide–alkyne cycloaddition

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Publication details

The article was received on 10 Mar 2012, accepted on 26 Apr 2012 and first published on 26 Apr 2012


Article type: Paper
DOI: 10.1039/C2DT30569K
Citation: Dalton Trans., 2012,41, 7660-7669
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    Functionalisation of lanthanide complexes via microwave-enhanced Cu(I)-catalysed azide–alkyne cycloaddition

    C. Szíjjártó, E. Pershagen and K. E. Borbas, Dalton Trans., 2012, 41, 7660
    DOI: 10.1039/C2DT30569K

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