A Benchtop Method for Appending Protic Functional Groups to N‐Heterocyclic Carbene Protected Gold Nanoparticles
- 24 February 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie
- Vol. 59 (19), 7585-7590
- https://doi.org/10.1002/anie.202001440
Abstract
The remarkable resilience of N‐heterocyclic carbene (NHC) gold bonds has quickly made NHCs the ligand of choice when functionalizing gold surfaces. Despite rapid progress using deposition from free or CO 2 ‐protected NHCs, synthetic challenges hinder the functionalization of NHC surfaces with protic functional groups, such as alcohols and amines, particularly on larger nanoparticles. Here, we synthesize NHC‐functionalized gold surfaces from gold(I) NHC complexes and aqueous nanoparticles without the need for additional reagents, enabling otherwise difficult functional groups to be appended to the carbene. The resilience of the NHC‐Au bond allows for multi‐step post‐synthetic modification. Beginning with the nitro‐NHC, we form an amine‐NHC terminated surface, which further undergoes amide coupling with carboxylic acids. The simplicity of this approach, its compatibility with aqueous nanoparticle solutions, and its ability to yield protic functionality, greatly expands the potential of NHC‐functionalized noble metal surfaces.Keywords
Funding Information
- National Science Foundation of Sri Lanka (CHE-1709881, CHE-1709468, CHE-1362825, NRT-1449785)
This publication has 52 references indexed in Scilit:
- Syntheses, Characterizations, and a Preliminary Comparative Cytotoxicity Study of Gold(I) and Gold(III) Complexes Bearing Benzimidazole- and Pyrazole-Derived N-Heterocyclic CarbenesOrganometallics, 2012
- A new strategy improves assembly efficiency of DNA mono-modified gold nanoparticlesChemical Communications, 2011
- Transmetalation of a Primary Amino-Functionalized N-Heterocyclic Carbene Ligand from an Axially Chiral Square-Planar Nickel(II) Complex to a Ruthenium(II) Precatalyst for the Transfer Hydrogenation of KetonesOrganometallics, 2009
- N-Heterocyclic carbene coated metal nanoparticlesNew Journal of Chemistry, 2009
- The hydrogenation of molecules with polar bonds catalyzed by a ruthenium(ii) complex bearing a chelating N-heterocyclic carbene with a primary amine donorChemical Communications, 2009
- Real-Time Glucose Sensing by Surface-Enhanced Raman Spectroscopy in Bovine Plasma Facilitated by a Mixed Decanethiol/Mercaptohexanol Partition LayerAnalytical Chemistry, 2005
- Air Oxidation of Self-Assembled Monolayers on Polycrystalline Gold: The Role of the Gold SubstrateLangmuir, 1998
- Darstellung, Struktur und Reaktivität von 1,3,4‐Triphenyl‐4,5‐dihydro‐1H‐1,2,4‐triazol‐5‐yliden, einem neuen stabilen CarbenAngewandte Chemie, 1995
- The Raman spectra of some aromatic nitro compoundsSpectrochimica Acta Part A: Molecular Spectroscopy, 1991
- Adsorption and surface-enhanced Raman of dyes on silver and gold solsThe Journal of Physical Chemistry, 1982