Sieving for gold-an efficient method for generating N-heterocyclic carbene self-assembled monolayers on nanostructured gold surfaces
Author(s)
Type
Journal Article
Abstract
N-Heterocyclic carbene self-assembled monolayers (NHC-SAMs) are an emerging class of ligands for metal surfaces with impressive chemical stability, proving vastly superior in specific applications compared to their thiol counterparts. Yet, unlike the latter, methods of forming such monolayers have poor functional group tolerability and require harsh or expensive reagents. Using a surface-enhanced Raman spectroscopy (SERS)-led optimization, we have developed a solution deposition methodology that relies on low-cost and easily accessible starting reagents. The addition of an external bicarbonate source greatly expanded the functional group tolerability, circumventing the need for the isolation of the benzimidazolium hydrogen carbonate. Additionally, inclusion of scavengers during the deposition, namely, molecular sieves (5 Å), improved monolayer formation and long-range ordering via the sequestration of CO2, a key side-product in the equilibrium between benzimidazolium salts with the hydrogen carbonate anion and their corresponding carbene. The methodology is operationally accessible, has broad functional group tolerability, and enables access to a wide substrate scope of NHCs using commonly available reagents.
Date Issued
2025-12-03
Date Acceptance
2025-10-31
Citation
Journal of the American Chemical Society, 2025, 147 (48), pp.44418-44429
ISSN
0002-7863
Publisher
American Chemical Society
Start Page
44418
End Page
44429
Journal / Book Title
Journal of the American Chemical Society
Volume
147
Issue
48
Copyright Statement
© 2025 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 .
License URL
Identifier
https://www.ncbi.nlm.nih.gov/pubmed/41251396
Subjects
ANCHORS
Chemistry
Chemistry, Multidisciplinary
COORDINATION
NANOPARTICLES
Physical Sciences
Science & Technology
Publication Status
Published
Coverage Spatial
United States
Date Publish Online
2025-11-18