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A Benchtop Method for Appending Protic Functional Groups to N‐Heterocyclic Carbene Protected Gold Nanoparticles
Author(s) -
DeJesus Joseph F.,
Sherman Lindy M.,
Yohannan Darius J.,
Becca Jeffrey C.,
Strausser Shelby L.,
Karger Leonhard F. P.,
Jensen Lasse,
Jenkins David M.,
Camden Jon P.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001440
Subject(s) - carbene , surface modification , combinatorial chemistry , chemistry , functional group , amide , colloidal gold , aqueous solution , amine gas treating , ligand (biochemistry) , nanoparticle , polymer chemistry , nanotechnology , organic chemistry , materials science , catalysis , biochemistry , receptor , polymer
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.