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Title: Breaking the paradigm: Record quindecim charged magnetic ionic liquids

Abstract

A family of bis(trifluoromethanesulfonyl)amide-based ionic liquids of composition [RE 5(C 2H 5-C 3H 3N 2-CH 2COO) 16(H 2O) 8](Tf 2N) 15 (RE = Er, Ho, Tm; C 3H 3N 2 ≡ imidazolium moiety) featuring the cationic, record quindecim {15+} charged pentanuclear rare earth (RE)-containing ion [RE 5(C 2H 5-C 3H 3N 2-CH 2COO) 16(H 2O) 8] 15+ has been synthesized and characterized. In addition, due to the presence of rare earth ions, these ionic liquids show a response to magnetic fields with the highest effective magnetic moment observed so far for an ionic liquid and are rare examples of ionic liquids showing luminescence in the near-infrared. As a result, these ionic liquids also were successfully employed in a three-component synthesis of 2-pyrrolo-3'-yloxindole with an extremely low (<0.035 mol%) catalyst loading rate.

Authors:
ORCiD logo [1];  [1];  [1];  [2];  [1];  [2]; ORCiD logo [2]
  1. Ames Lab., Ames, IA (United States)
  2. Ames Lab. and Iowa State Univ., Ames, IA (United States)
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1357792
Report Number(s):
IS-J-9311
Journal ID: ISSN 2051-6347; MHAOAL; TRN: US1702303
Grant/Contract Number:  
CHE-1465071; AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Materials Horizons
Additional Journal Information:
Journal Volume: 4; Journal Issue: 2; Journal ID: ISSN 2051-6347
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Prodius, D., Smetana, V., Steinberg, S., Wilk-Kozubek, M., Mudryk, Y., Pecharsky, V. K., and Mudring, A. -V. Breaking the paradigm: Record quindecim charged magnetic ionic liquids. United States: N. p., 2016. Web. doi:10.1039/C6MH00468G.
Prodius, D., Smetana, V., Steinberg, S., Wilk-Kozubek, M., Mudryk, Y., Pecharsky, V. K., & Mudring, A. -V. Breaking the paradigm: Record quindecim charged magnetic ionic liquids. United States. doi:10.1039/C6MH00468G.
Prodius, D., Smetana, V., Steinberg, S., Wilk-Kozubek, M., Mudryk, Y., Pecharsky, V. K., and Mudring, A. -V. Thu . "Breaking the paradigm: Record quindecim charged magnetic ionic liquids". United States. doi:10.1039/C6MH00468G. https://www.osti.gov/servlets/purl/1357792.
@article{osti_1357792,
title = {Breaking the paradigm: Record quindecim charged magnetic ionic liquids},
author = {Prodius, D. and Smetana, V. and Steinberg, S. and Wilk-Kozubek, M. and Mudryk, Y. and Pecharsky, V. K. and Mudring, A. -V.},
abstractNote = {A family of bis(trifluoromethanesulfonyl)amide-based ionic liquids of composition [RE5(C2H5-C3H3N2-CH2COO)16(H2O)8](Tf2N)15 (RE = Er, Ho, Tm; C3H3N2 ≡ imidazolium moiety) featuring the cationic, record quindecim {15+} charged pentanuclear rare earth (RE)-containing ion [RE5(C2H5-C3H3N2-CH2COO)16(H2O)8]15+ has been synthesized and characterized. In addition, due to the presence of rare earth ions, these ionic liquids show a response to magnetic fields with the highest effective magnetic moment observed so far for an ionic liquid and are rare examples of ionic liquids showing luminescence in the near-infrared. As a result, these ionic liquids also were successfully employed in a three-component synthesis of 2-pyrrolo-3'-yloxindole with an extremely low (<0.035 mol%) catalyst loading rate.},
doi = {10.1039/C6MH00468G},
journal = {Materials Horizons},
number = 2,
volume = 4,
place = {United States},
year = {2016},
month = {12}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

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Cited by: 6 works
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Figures / Tables:

Figure 1 Figure 1: Images of ionic liquids after a two month crystallization term: {Er5} (1, middle), {Ho5} (2, left) and {Tm5} (3, right) and their TG (solid line)/DSC (dotted line) curves (for crystalline 1; for 2 and 3 in a liquid state).

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    Works referencing / citing this record:

    Breaking the paradigm: record quindecim charged magnetic ionic liquids
    text, January 2017


    Bei Raumtemperatur flüssige ionische Verbindungen auf Dysprosium-Basis mit starker Lumineszenz und Reaktion auf magnetische Felder
    journal, September 2008

    • Mallick, Bert; Balke, Benjamin; Felser, Claudia
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    • DOI: 10.1002/ange.200802390

    Isocyanide in der Synthese von Stickstoff-Heterocyclen
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    Ionic Liquids for the Convenient Synthesis of Functional Nanoparticles and Other Inorganic Nanostructures
    journal, September 2004

    • Antonietti, Markus; Kuang, Daibin; Smarsly, Bernd
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    • DOI: 10.1002/anie.200460091

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    • Tang, Sifu; Babai, Arash; Mudring, Anja-Verena
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    • DOI: 10.1002/anie.200801159

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    • Groom, Colin R.; Allen, Frank H.
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    Energetic Ionic Liquids based on Lanthanide Nitrate Complex Anions
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    • Tao, Guo-Hong; Huang, Yangen; Boatz, Jerry A.
    • Chemistry - A European Journal, Vol. 14, Issue 35
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    • European Journal of Inorganic Chemistry, Vol. 2005, Issue 23
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    • Tang, Si-Fu; Mudring, Anja-Verena
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    • DOI: 10.1002/ejic.200900114

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    • Getsis, Anna; Tang, Sifu; Mudring, Anja-Verena
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    • European Journal of Organic Chemistry, Vol. 2011, Issue 8
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    Luminescent Soft Material: Two New Europium-Based Ionic Liquids
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    • Tang, Sifu; Cybinska, Joanna; Mudring, Anja-Verena
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    journal, May 2008

    • Babai, Arash; Mudring, Anja-Verena
    • Zeitschrift für anorganische und allgemeine Chemie, Vol. 634, Issue 5
    • DOI: 10.1002/zaac.200700545

    Ionic Liquids
    journal, December 1999

    • Holbrey, J. D.; Seddon, K. R.
    • Clean Technologies and Environmental Policy, Vol. 1, Issue 4
    • DOI: 10.1007/s100980050036

    Magnetic ionic liquids in analytical chemistry: A review
    journal, August 2016


    Intense near-infrared luminescence of anhydrous lanthanide(III) iodides in an imidazolium ionic liquid
    journal, January 2005


    InCl3-catalyzed efficient one-pot synthesis of 2-pyrrolo-3′-yloxindoles
    journal, July 2009


    Spectral and Physicochemical Characterization of Dysprosium-Based Multifunctional Ionic Liquid Crystals
    journal, May 2015

    • Lu, Chengfei; Das, Susmita; Siraj, Noureen
    • The Journal of Physical Chemistry A, Vol. 119, Issue 20
    • DOI: 10.1021/acs.jpca.5b01180

    Easily Accessible Rare-Earth-Containing Phosphonium Room-Temperature Ionic Liquids: EXAFS, Luminescence, and Magnetic Properties
    journal, May 2016

    • Alvarez-Vicente, Jorge; Dandil, Sahra; Banerjee, Dipanjan
    • The Journal of Physical Chemistry B, Vol. 120, Issue 23
    • DOI: 10.1021/acs.jpcb.6b03870

    Dysprosium-Based Ionic Liquid Crystals: Thermal, Structural, Photo- and Magnetophysical Properties
    journal, October 2009

    • Getsis, Anna; Balke, Benjamin; Felser, Claudia
    • Crystal Growth & Design, Vol. 9, Issue 10
    • DOI: 10.1021/cg900463b

    Synthetic Strategies for Tailoring the Physicochemical and Magnetic Properties of Hydrophobic Magnetic Ionic Liquids
    journal, January 2015

    • Nacham, Omprakash; Clark, Kevin D.; Yu, Honglian
    • Chemistry of Materials, Vol. 27, Issue 3
    • DOI: 10.1021/cm504202v

    Ionic Liquids in Heterocyclic Synthesis
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    • DOI: 10.1021/cr078399y

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    • Chemical Reviews, Vol. 110, Issue 3
    • DOI: 10.1021/cr900204u

    Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis
    journal, August 1999

    • Welton, Thomas
    • Chemical Reviews, Vol. 99, Issue 8, p. 2071-2084
    • DOI: 10.1021/cr980032t

    Crystal Engineering in Ionic Liquids. The Crystal Structures of [Mppyr] 3 [NdI 6 ] and [Bmpyr] 4 [NdI 6 ][Tf 2 N]
    journal, June 2006

    • Babai, Arash; Mudring, Anja-Verena
    • Inorganic Chemistry, Vol. 45, Issue 13
    • DOI: 10.1021/ic060414e

    Europium(III) Tetrakis(β-diketonate) Complex as an Ionic Liquid: A Calorimetric and Spectroscopic Study
    journal, June 2012

    • Pereira, Cláudia C. L.; Dias, Sofia; Coutinho, Isabel
    • Inorganic Chemistry, Vol. 52, Issue 7
    • DOI: 10.1021/ic3023024

    Anionic Rare-Earth Thiocyanate Complexes as Building Blocks for Low-Melting Metal-Containing Ionic Liquids
    journal, October 2006

    • Nockemann, Peter; Thijs, Ben; Postelmans, Niels
    • Journal of the American Chemical Society, Vol. 128, Issue 42
    • DOI: 10.1021/ja0640391

    The first homoleptic bis(trifluoromethanesulfonyl)amide complex compounds of trivalent f-elements
    journal, January 2006

    • Babai, Arash; Mudring, Anja-Verena
    • Dalton Transactions, Issue 15
    • DOI: 10.1039/b517694h

    Towards large-scale, fully ab initio calculations of ionic liquids
    journal, January 2011

    • Izgorodina, Ekaterina I.
    • Physical Chemistry Chemical Physics, Vol. 13, Issue 10
    • DOI: 10.1039/c0cp02315a

    Recent advances in asymmetric catalysis with cinchona alkaloid-based primary amines
    journal, January 2011

    • Jiang, Lin; Chen, Ying-Chun
    • Catalysis Science & Technology, Vol. 1, Issue 3
    • DOI: 10.1039/c0cy00096e

    Catalytic “triangles”: binding of iron in task-specific ionic liquids
    journal, January 2013

    • Prodius, Denis; Macaev, Fliur; Stingaci, Eugenia
    • Chemical Communications, Vol. 49, Issue 19
    • DOI: 10.1039/c2cc36741f

    Evidence of slow relaxation of magnetization in dysprosium-based ionic liquids
    journal, January 2013

    • Prodius, Denis; Macaev, Fliur; Lan, Yanhua
    • Chemical Communications, Vol. 49, Issue 80
    • DOI: 10.1039/c3cc45554h

    Crystal structure of Zn(ZnCl 4 ) 2 (Cho) 2 : the transformation of ions to neutral species in a deep eutectic system
    journal, January 2017

    • Patil, Yogesh P.; Kore, Rajkumar; Kelley, Steven P.
    • Chemical Communications, Vol. 53, Issue 39
    • DOI: 10.1039/c7cc01754e

    Influence of lanthanides on spin-relaxation and spin-structure in a family of Fe 7 Ln 4 single molecule magnets
    journal, January 2018

    • Prodius, Denis; Mereacre, Valeriu; Singh, Prashant
    • Journal of Materials Chemistry C, Vol. 6, Issue 11
    • DOI: 10.1039/c8tc00322j

    Quenching of Er(III) luminescence by ligand C–H vibrations: Implications for the use of erbium complexes in telecommunications
    journal, September 2006

    • Winkless, L.; Tan, R. H. C.; Zheng, Y.
    • Applied Physics Letters, Vol. 89, Issue 11
    • DOI: 10.1063/1.2345909

    Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride
    journal, May 2018

    • Prodius, Denis; Wilk-Kozubek, Magdalena; Mudring, Anja-Verena
    • Acta Crystallographica Section C Structural Chemistry, Vol. 74, Issue 6
    • DOI: 10.1107/s2053229618005272

    Discovery of a Magnetic Ionic Liquid [bmim]FeCl 4
    journal, December 2004

    • Hayashi, Satoshi; Hamaguchi, Hiro-o
    • Chemistry Letters, Vol. 33, Issue 12
    • DOI: 10.1246/cl.2004.1590

    Triethylamine-templated nanocalix Ln 12 clusters of diacylhydrazone: crystal structures and magnetic properties
    journal, January 2019

    • Luo, Zhi-Rong; Zou, Hua-Hong; Chen, Zi-Lu
    • Dalton Transactions, Vol. 48, Issue 46
    • DOI: 10.1039/c9dt03335a

    Ectonucleotidase Inhibitory and Redox Activity of Imidazole-Based Organic Salts and Ionic Liquids
    journal, October 2018

    • Boldescu, Veaceslav; Sucman, Natalia; Hassan, Sidra
    • ChemMedChem, Vol. 13, Issue 21
    • DOI: 10.1002/cmdc.201800520

    Crystal structure of Zn(ZnCl 4 ) 2 (Cho) 2 : the transformation of ions to neutral species in a deep eutectic system
    journal, January 2017

    • Patil, Yogesh P.; Kore, Rajkumar; Kelley, Steven P.
    • Chemical Communications, Vol. 53, Issue 39
    • DOI: 10.1039/c7cc01754e

    Influence of lanthanides on spin-relaxation and spin-structure in a family of Fe 7 Ln 4 single molecule magnets
    journal, January 2018

    • Prodius, Denis; Mereacre, Valeriu; Singh, Prashant
    • Journal of Materials Chemistry C, Vol. 6, Issue 11
    • DOI: 10.1039/c8tc00322j

    Triethylamine-templated nanocalix Ln 12 clusters of diacylhydrazone: crystal structures and magnetic properties
    journal, January 2019

    • Luo, Zhi-Rong; Zou, Hua-Hong; Chen, Zi-Lu
    • Dalton Transactions, Vol. 48, Issue 46
    • DOI: 10.1039/c9dt03335a

    Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride
    journal, May 2018

    • Prodius, Denis; Wilk-Kozubek, Magdalena; Mudring, Anja-Verena
    • Acta Crystallographica Section C Structural Chemistry, Vol. 74, Issue 6
    • DOI: 10.1107/s2053229618005272

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.