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Issue 27, 2015
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Covalent attachment of diphosphine ligands to glassy carbon electrodes via Cu-catalyzed alkyne-azide cycloaddition. Metallation with Ni(II)

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Abstract

Covalent tethering of PPh2NC6H4C[triple bond, length as m-dash]CH2 ligands (PPh2NC6H4C[triple bond, length as m-dash]CH2 = 1,5-di-(4-ethynylphenyl)-3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane) to planar, azide-terminated glassy carbon electrode surfaces has been accomplished using a CuI-catalyzed alkyne-azide cycloaddition (CuAAC) coupling reaction, using a BH3←P protection-deprotection strategy. Deprotected, surface-confined ligands were metallated using [NiII(MeCN)6](BF4)2. X-ray photoelectron spectroscopic measurements demonstrate that metallation introduced 1.3 equivalents NiII per diphosphine onto the electrode surface. Exposure of the surface to a second diphosphine ligand, PPh2NPh2, resulted in the removal of Ni from the surface. Protection, coupling, deprotection, and metallation conditions were optimized using solution-phase model systems, with benzyl azide as a model for the azide-terminated carbon surface; these reactions generate a [NiII(diphosphine)2]2+ complex.

Graphical abstract: Covalent attachment of diphosphine ligands to glassy carbon electrodes via Cu-catalyzed alkyne-azide cycloaddition. Metallation with Ni(ii)

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Publication details

The article was received on 14 Jan 2015, accepted on 17 Mar 2015 and first published on 17 Mar 2015


Article type: Paper
DOI: 10.1039/C5DT00162E
Author version available: Download Author version (PDF)
Citation: Dalton Trans., 2015,44, 12225-12233
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    Covalent attachment of diphosphine ligands to glassy carbon electrodes via Cu-catalyzed alkyne-azide cycloaddition. Metallation with Ni(II)

    A. K. Das, M. H. Engelhard, S. Lense, J. A. S. Roberts and R. M. Bullock, Dalton Trans., 2015, 44, 12225
    DOI: 10.1039/C5DT00162E

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