Grignard functionalization of weinreb amide-modified Au nanoparticles

Christopher J. Thode, Mary Elizabeth Williams

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Reactions of Grignard and organolithium reagents are staple transformations in organic chemistry. However, their use in the chemical functionalization of monolayer-protected metallic nanoparticles is unprecedented. In this letter, we report the reaction of Au nanoparticles bearing a mixed monolayer of alkanethiol ligands that are methyl- and N-methoxy-N-methyl amide-terminated. The latter of these rapidly undergoes reaction with organometallic reagents, achieving high yields (in some cases, nearly quantitative) in only a few hours without the need for high pressure, temperature or catalysts. We assess the feasibility of this reaction with a range of organometallic reagents on the basis of both surface reaction yield and also the stability of the particles (defined as the mass % Au particles recovered vs a control). Demonstrating the utility of these strong organometallic reagents opens the door to a large class of reactions that are underutilized within the field of nanomaterials.

Original languageEnglish (US)
Pages (from-to)5988-5990
Number of pages3
JournalLangmuir
Volume24
Issue number12
DOIs
StatePublished - Jun 17 2008

Fingerprint

Organometallics
Amides
amides
reagents
Nanoparticles
nanoparticles
Monolayers
Bearings (structural)
Surface reactions
Nanostructured materials
organic chemistry
Ligands
particle mass
Catalysts
surface reactions
catalysts
ligands
Temperature
temperature

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

Cite this

Thode, Christopher J. ; Williams, Mary Elizabeth. / Grignard functionalization of weinreb amide-modified Au nanoparticles. In: Langmuir. 2008 ; Vol. 24, No. 12. pp. 5988-5990.
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Grignard functionalization of weinreb amide-modified Au nanoparticles. / Thode, Christopher J.; Williams, Mary Elizabeth.

In: Langmuir, Vol. 24, No. 12, 17.06.2008, p. 5988-5990.

Research output: Contribution to journalArticle

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