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 language | English |
|---|---|
| Pages (from-to) | 13674-13684 |
| Number of pages | 11 |
| Journal | Inorganic Chemistry |
| Volume | 52 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - Dec 2 2013 |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Physical and Theoretical Chemistry
Cite this
The electrode as organolithium reagent : Catalyst-free covalent attachment of electrochemically active species to an azide-terminated glassy carbon electrode surface. / Das, Atanu K.; Engelhard, Mark H.; Liu, Fei; Bullock, R Morris; Roberts, John.
In: Inorganic Chemistry, Vol. 52, No. 23, 02.12.2013, p. 13674-13684.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The electrode as organolithium reagent
T2 - Catalyst-free covalent attachment of electrochemically active species to an azide-terminated glassy carbon electrode surface
AU - Das, Atanu K.
AU - Engelhard, Mark H.
AU - Liu, Fei
AU - Bullock, R Morris
AU - Roberts, John
PY - 2013/12/2
Y1 - 2013/12/2
N2 - 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.
AB - 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.
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U2 - 10.1021/ic402247n
DO - 10.1021/ic402247n
M3 - Article
VL - 52
SP - 13674
EP - 13684
JO - Inorganic Chemistry
JF - Inorganic Chemistry
SN - 0020-1669
IS - 23
ER -