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

Abstract

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.

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

Citation Formats

Rutledge, Ryan D, Warner, Cynthia L, Pittman, Jonathan W, Addleman, Raymond S, Engelhard, Mark H, Chouyyok, Wilaiwan, and Warner, Marvin G. Thiol-Ene Induced Diphosphonic Acid Functionalization of Superparamagnetic Iron Oxide Nanoparticles. United States: N. p., 2010. Web. doi:10.1021/la101362y.
Rutledge, Ryan D, Warner, Cynthia L, Pittman, Jonathan W, Addleman, Raymond S, Engelhard, Mark H, Chouyyok, Wilaiwan, & Warner, Marvin G. Thiol-Ene Induced Diphosphonic Acid Functionalization of Superparamagnetic Iron Oxide Nanoparticles. United States. https://doi.org/10.1021/la101362y
Rutledge, Ryan D, Warner, Cynthia L, Pittman, Jonathan W, Addleman, Raymond S, Engelhard, Mark H, Chouyyok, Wilaiwan, and Warner, Marvin G. 2010. "Thiol-Ene Induced Diphosphonic Acid Functionalization of Superparamagnetic Iron Oxide Nanoparticles". United States. https://doi.org/10.1021/la101362y.
@article{osti_988120,
title = {Thiol-Ene Induced Diphosphonic Acid Functionalization of Superparamagnetic Iron Oxide Nanoparticles},
author = {Rutledge, Ryan D and Warner, Cynthia L and Pittman, Jonathan W and Addleman, Raymond S and Engelhard, Mark H and Chouyyok, Wilaiwan and Warner, Marvin G},
abstractNote = {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.},
doi = {10.1021/la101362y},
url = {https://www.osti.gov/biblio/988120}, journal = {Langmuir, 26(14):12285-12292},
issn = {0743-7463},
number = 14,
volume = 26,
place = {United States},
year = {Tue Jul 20 00:00:00 EDT 2010},
month = {Tue Jul 20 00:00:00 EDT 2010}
}