Thiol-Ene Induced Diphosphonic Acid Functionalization of Superparamagnetic Iron Oxide Nanoparticles

Journal Article · Tue Jul 20 00:00:00 EDT 2010 · Langmuir, 26(14):12285-12292

DOI:https://doi.org/10.1021/la101362y· OSTI ID:988120

Rutledge, Ryan D; Warner, Cynthia L; Pittman, Jonathan W; Addleman, Raymond S; Engelhard, Mark H; Chouyyok, Wilaiwan; Warner, Marvin G

Multi-functional organic molecules represent an interesting challenge for nanoparticle functionalization due to the potential for undesirable interactions between the substrate material and the variable functionalities, making it difficult to control the final orientation of the ligand. In the present study, UV-induced thiol-ene click chemistry has been utilized as a means of directed functionalization of bifunctional ligands on an iron oxide nanoparticle surface. Allyl diphosphonic acid ligand was covalently deposited on the surface of thiol-presenting iron oxide nanoparticles via the formation of a UV-induced thioether. This method of thiol-ene click chemistry offers a set of reaction conditions capable of controlling the ligand deposition and circumventing the natural affinity exhibited by the phosphonic acid moiety for the iron oxide surface. These claims are supported via a multimodal characterization platform which includes thermogravimetric analysis, x-ray photoelectron spectroscopy, and metal contact analysis and are consistent with a properly oriented, highly active ligand on the nanoparticle surface. These experiments suggest thiol-ene click chemistry as both a practical and generally applicable strategy for the directed deposition of multi-functional ligands on metal oxide nanoparticle surfaces.

• Research Organization: Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Environmental Molecular Sciences Lab. (EMSL)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 988120
• Report Number(s): PNNL-SA-71652; ISSN 1520-5827; 30400; 400412000; TRN: US201018%%130
• Journal Information: Langmuir, 26(14):12285-12292, Vol. 26, Issue 14; ISSN 0743-7463
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
IRON OXIDES
PHOSPHONIC ACIDS
SUBSTRATES
THERMAL GRAVIMETRIC ANALYSIS
X-RAY PHOTOELECTRON SPECTROSCOPY
NANOSTRUCTURES
THIOLS
ULTRAVIOLET RADIATION
LIGANDS
DEPOSITION
iron oxide nanoparticle
thiol-ene click chemistry
sorbent
diphosphonic acid
Environmental Molecular Sciences Laboratory