Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 27, 2015
Previous Article Next Article

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

Author affiliations

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)

Back to tab navigation
Please wait while Download options loads

Supplementary files

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
Citation: Dalton Trans., 2015,44, 12225-12233
  •   Request permissions

    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

Search articles by author