The electrode as organolithium reagent: Catalyst-free covalent attachment of electrochemically active species to an azide-terminated glassy carbon electrode surface

Atanu K. Das, Mark H. Engelhard, Fei Liu, R Morris Bullock, John Roberts

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Abstract

The reaction of a lithium acetylide-ethylenediamine complex with azide-terminated glassy carbon surfaces affords 1,2,3-triazolyllithium surface groups that are active toward covalent C-C coupling reactions, including salt metathesis with an aliphatic halide and nucleophilic addition at an aldehyde. Surface ferrocenyl groups were introduced by reaction with (6-iodohexyl) ferrocene; the voltammetry of electrode samples shows narrow, symmetric peaks indicating uniform attachment. X-ray photoelectron and reflectance infrared spectroscopic data provide further support for the surface-attached products. Formation of the 1,2,3-triazolyllithium linkage requires neither a catalyst nor a strained alkyne. Coverages obtained by this route are similar to those obtained by the more common Cu(I)-catalyzed alkyne-azide coupling (CuAAC) of ethynylferrocene with surface azides. Preconditioning of the glassy carbon disk electrodes at ambient temperature under nitrogen affords coverages comparable to those reported with preconditioning at 1000 C under hydrogen/nitrogen.

Original languageEnglish
Pages (from-to)13674-13684
Number of pages11
JournalInorganic Chemistry
Volume52
Issue number23
DOIs
Publication statusPublished - Dec 2 2013

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ASJC Scopus subject areas

  • Inorganic Chemistry
  • Physical and Theoretical Chemistry

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