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Amphiphilic N-Heterocyclic Carbene-Stabilized Gold Nanoparticles and Their Self-Assembly in Polar Solvents
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    Amphiphilic N-Heterocyclic Carbene-Stabilized Gold Nanoparticles and Their Self-Assembly in Polar Solvents
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    Department of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario K7L 3N6, Canada
    Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
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    Langmuir

    Cite this: Langmuir 2017, 33, 50, 14211–14219
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    https://doi.org/10.1021/acs.langmuir.7b02248
    Published November 17, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    Soft matter-directed self-assembly of amphiphilic inorganic nanoparticles (NPs) has recently emerged as a promising approach to access NP ensembles with superior collective properties. While thiol-terminated molecules are primarily employed to tether the amphiphilic ligand to the metal, concerns remain regarding the stabilities of the resulting NPs and their corresponding aggregates. As an alternative, we report amphiphilic N-heterocyclic carbene (NHC)-functionalized gold nanoparticles (AuNPs). To accomplish this, an amphiphilic NHC-AuI complex based on an asymmetric triethylene glycol-/dodecyl-functionalized benzimidazole was first synthesized and used to prepare the corresponding stable amphiphilic NHC-decorated AuNPs. The resulting NPs were comprehensively characterized using both solution- and solid-state-based techniques such as proton nuclear magnetic resonance spectroscopy, dynamic light scattering, transmission electron microscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy. By optimizing the self-assembly behavior of these amphiphilic AuNPs in deionized water, ethanol, and their mixtures, we were able to fine-tune the plasmonic properties of the AuNPs in the wide range of 525–640 nm. Furthermore, when treated with thiols, the ensembles showed greater stability compared to their parent discrete AuNP counterparts at room temperature.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.langmuir.7b02248.

    • NMR spectra; COSY spectrum; TEM micrographs; UV–vis spectra; XPS spectra; TGA curves (PDF)

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    Cited By

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    13. Constantin Eisen, Bernhard K. Keppler, Jia Min Chin, Xiaodi Su, Michael R. Reithofer. Fabrication of azido-PEG-NHC stabilized gold nanoparticles as a functionalizable platform. Chemical Science 2024, 15 (44) , 18524-18533. https://doi.org/10.1039/D4SC04112G
    14. Nathaniel Ukah, Hermann A. Wegner. On-surface synthesis – Ullmann coupling reactions on N-heterocyclic carbene functionalized gold nanoparticles. Nanoscale 2024, 16 (39) , 18524-18533. https://doi.org/10.1039/D4NR03065F
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    43. David Ventura-Espinosa, Santiago Martín, Jose A. Mata. The non-innocent role of graphene in the formation/immobilization of ultra-small gold nanoparticles functionalized with N-heterocyclic carbene ligands. Journal of Catalysis 2019, 375 , 419-426. https://doi.org/10.1016/j.jcat.2019.06.009
    44. Adam J. Young, Markus Sauer, Guilherme M. D. M. Rubio, Akiko Sato, Annette Foelske, Christopher J. Serpell, Jia Min Chin, Michael R. Reithofer. One-step synthesis and XPS investigations of chiral NHC–Au(0)/Au( i ) nanoparticles. Nanoscale 2019, 11 (17) , 8327-8333. https://doi.org/10.1039/C9NR00905A
    45. Yuan‐Yuan An, Jian‐Gang Yu, Ying‐Feng Han. Recent Advances in the Chemistry of N ‐Heterocyclic‐Carbene‐Functionalized Metal‐Nanoparticles and Their Applications. Chinese Journal of Chemistry 2019, 37 (1) , 76-87. https://doi.org/10.1002/cjoc.201800450
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    Langmuir

    Cite this: Langmuir 2017, 33, 50, 14211–14219
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.langmuir.7b02248
    Published November 17, 2017
    Copyright © 2017 American Chemical Society

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