Investigating the effect of ligand and cation on the properties of metal fluorinated acetylacetonate based magnetic ionic liquids
Abstract
Magnetic ionic liquids (MILs) are a subclass of ionic liquids that possess a paramagnetic metal within their chemical structure, making them susceptible to external magnetic fields. A total of twenty-four (24) MILs were prepared and characterized to investigate the effect of the ligand, cation and anion on the physiochemical properties of acetylacetonate-based MILs. It was found that thermal stabilities as high as 260 °C could be achieved by incorporating aromatic moieties in the anion structure. Additionally, the magnetic moment could be modulated by simply changing the transition metal in the anion. Magnetic moment values of 2.8 μB, 4.5 μB and 5.6 μB were obtained by using Ni(II), Co(II), and Mn(II) as the metal centers, respectively. Furthermore, the viscosity of the MILs could be tailored from a few hundred centipoise to several thousand centipoise, increasing their potential applications in numerous interdisciplinary fields. Moreover, the MILs synthesized in this study were found to be insoluble in water at a MIL-to-solvent ratio of 0.01% (w/v), making them potentially useful in targeted separations, where very hydrophobic solvents are highly desired.
- Authors:
-
- Department of Chemistry, Iowa State University, Ames, USA
- Division of Materials Science and Engineering, Ames Laboratory, Iowa State University, Ames, USA
- Publication Date:
- Research Org.:
- Ames Lab., Ames, IA (United States)
- Sponsoring Org.:
- USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division
- OSTI Identifier:
- 1530898
- Alternate Identifier(s):
- OSTI ID: 1556104
- Report Number(s):
- IS-J-9988
Journal ID: ISSN 1144-0546; NJCHE5
- Grant/Contract Number:
- AC02-07CH11358; CHE-1709372
- Resource Type:
- Published Article
- Journal Name:
- New Journal of Chemistry
- Additional Journal Information:
- Journal Name: New Journal of Chemistry Journal Volume: 43 Journal Issue: 28; Journal ID: ISSN 1144-0546
- Publisher:
- Royal Society of Chemistry (RSC)
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE
Citation Formats
Farooq, Muhammad Qamar, Chand, Deepak, Odugbesi, Gabriel A., Varona, Marcelino, Mudryk, Yaroslav, and Anderson, Jared L. Investigating the effect of ligand and cation on the properties of metal fluorinated acetylacetonate based magnetic ionic liquids. United Kingdom: N. p., 2019.
Web. doi:10.1039/C9NJ02595B.
Farooq, Muhammad Qamar, Chand, Deepak, Odugbesi, Gabriel A., Varona, Marcelino, Mudryk, Yaroslav, & Anderson, Jared L. Investigating the effect of ligand and cation on the properties of metal fluorinated acetylacetonate based magnetic ionic liquids. United Kingdom. https://doi.org/10.1039/C9NJ02595B
Farooq, Muhammad Qamar, Chand, Deepak, Odugbesi, Gabriel A., Varona, Marcelino, Mudryk, Yaroslav, and Anderson, Jared L. Mon .
"Investigating the effect of ligand and cation on the properties of metal fluorinated acetylacetonate based magnetic ionic liquids". United Kingdom. https://doi.org/10.1039/C9NJ02595B.
@article{osti_1530898,
title = {Investigating the effect of ligand and cation on the properties of metal fluorinated acetylacetonate based magnetic ionic liquids},
author = {Farooq, Muhammad Qamar and Chand, Deepak and Odugbesi, Gabriel A. and Varona, Marcelino and Mudryk, Yaroslav and Anderson, Jared L.},
abstractNote = {Magnetic ionic liquids (MILs) are a subclass of ionic liquids that possess a paramagnetic metal within their chemical structure, making them susceptible to external magnetic fields. A total of twenty-four (24) MILs were prepared and characterized to investigate the effect of the ligand, cation and anion on the physiochemical properties of acetylacetonate-based MILs. It was found that thermal stabilities as high as 260 °C could be achieved by incorporating aromatic moieties in the anion structure. Additionally, the magnetic moment could be modulated by simply changing the transition metal in the anion. Magnetic moment values of 2.8 μB, 4.5 μB and 5.6 μB were obtained by using Ni(II), Co(II), and Mn(II) as the metal centers, respectively. Furthermore, the viscosity of the MILs could be tailored from a few hundred centipoise to several thousand centipoise, increasing their potential applications in numerous interdisciplinary fields. Moreover, the MILs synthesized in this study were found to be insoluble in water at a MIL-to-solvent ratio of 0.01% (w/v), making them potentially useful in targeted separations, where very hydrophobic solvents are highly desired.},
doi = {10.1039/C9NJ02595B},
journal = {New Journal of Chemistry},
number = 28,
volume = 43,
place = {United Kingdom},
year = {Mon Jul 15 00:00:00 EDT 2019},
month = {Mon Jul 15 00:00:00 EDT 2019}
}
https://doi.org/10.1039/C9NJ02595B
Web of Science
Works referenced in this record:
Magnetic ionic liquids based on transition metal complexes with N -alkylimidazole ligands
journal, January 2019
- Chand, Deepak; Farooq, Muhammad Qamar; Pathak, Arjun K.
- New Journal of Chemistry, Vol. 43, Issue 1
Synthesis and characterization of Magnetic Ionic Liquids (MILs) for CO 2 separation
journal, May 2014
- Santos, Esther; Albo, Jonathan; Rosatella, Andreia
- Journal of Chemical Technology & Biotechnology, Vol. 89, Issue 6
Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2
journal, May 2011
- Hallett, Jason P.; Welton, Tom
- Chemical Reviews, Vol. 111, Issue 5
Thermophysical and magnetic studies of two paramagnetic liquid salts: [C4mim][FeCl4] and [P66614][FeCl4]
journal, July 2013
- Cruz, M. M.; Borges, R. P.; Godinho, M.
- Fluid Phase Equilibria, Vol. 350
Trigonal Tricationic Ionic Liquids: A Generation of Gas Chromatographic Stationary Phases
journal, January 2009
- Payagala, Tharanga; Zhang, Ying; Wanigasekara, Eranda
- Analytical Chemistry, Vol. 81, Issue 1
Solubility and phase behavior of binary systems containing salts based on transitional metals
journal, August 2013
- Zakrzewska, Małgorzata E.; Paninho, Ana B.; Môlho, Marta F.
- The Journal of Chemical Thermodynamics, Vol. 63
Ionic Liquids for Clean Technology
journal, April 1997
- Seddon, Kenneth R.
- Journal of Chemical Technology & Biotechnology, Vol. 68, Issue 4
Physicochemical characterization of paramagnetic ionic liquids 1-vinyl-3-alkylimidazolium tetrahalogenidoferrate(III) [VRIM][FeCl m Br 4 − m ] : PHYSICOCHEMICAL CHARACTERIZATION OF PARAMAGNETIC IONIC LIQUIDS
journal, February 2014
- Tang, Yimei; Hu, Xiaoling; Guan, Ping
- Journal of Physical Organic Chemistry, Vol. 27, Issue 6
Tetraalkylphosphonium-based ionic liquids
journal, May 2005
- Del Sesto, Rico E.; Corley, Cynthia; Robertson, Al
- Journal of Organometallic Chemistry, Vol. 690, Issue 10, p. 2536-2542
Extractive Desulfurization Using Fe-Containing Ionic Liquids
journal, May 2008
- Ko, Nan Hee; Lee, Je Seung; Huh, Eun Soo
- Energy & Fuels, Vol. 22, Issue 3
Dication magnetic ionic liquids with tuneable heteroanions
journal, January 2013
- Brown, Paul; Butts, Craig P.; Eastoe, Julian
- Chemical Communications, Vol. 49, Issue 27
A new class of magnetic fluids: bmim[FeCl/sub 4/] and nbmim[FeCl/sub 4/] ionic liquids
journal, January 2006
- Hayashi, S.; Saha, S.; Hamaguchi, H.
- IEEE Transactions on Magnetics, Vol. 42, Issue 1
Sonochemical formation of iron oxide nanoparticles in ionic liquids for magnetic liquid marble
journal, January 2012
- Zhang, Shiguo; Zhang, Yan; Wang, Ying
- Physical Chemistry Chemical Physics, Vol. 14, Issue 15
Trigonal-Prismatic vs. Octahedral Geometry for MnII Complexes with Innocent Didentate Ligands: A Subtle Difference as Shown by XRD and DFT on [Mn(acac)2(bpy)]
journal, June 2005
- van Gorkum, Remy; Buda, Francesco; Kooijman, Huub
- European Journal of Inorganic Chemistry, Vol. 2005, Issue 11
Paramagnetic Ionic Liquids for Measurements of Density Using Magnetic Levitation
journal, August 2013
- Bwambok, David K.; Thuo, Martin M.; Atkinson, Manza B. J.
- Analytical Chemistry, Vol. 85, Issue 17
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
Design of functional ionic liquids using magneto- and luminescent-active anions
journal, January 2010
- Yoshida, Yukihiro; Saito, Gunzi
- Phys. Chem. Chem. Phys., Vol. 12, Issue 8
Metallocenium Ionic Liquids
journal, June 2010
- Inagaki, Takashi; Mochida, Tomoyuki
- Chemistry Letters, Vol. 39, Issue 6
Friedel-Crafts acylation of aromatics catalysed by supported ionic liquids
journal, July 2001
- Valkenberg, M. H.; deCastro, C.; Hölderich, W. F.
- Applied Catalysis A: General, Vol. 215, Issue 1-2
Influence of structural variations in 1-alkyl-3-methylimidazolium cation and tetrahalogenoferrate(iii) anion on the physical properties of the paramagnetic ionic liquids
journal, January 2006
- Yoshida, Yukihiro; Saito, Gunzi
- Journal of Materials Chemistry, Vol. 16, Issue 13
Ionic liquids with metal chelate anions
journal, January 2012
- Zhang, Pengfei; Gong, Yutong; Lv, Yiqi
- Chemical Communications, Vol. 48, Issue 17
Synthesis and characterization of low viscosity hexafluoroacetylacetonate-based hydrophobic magnetic ionic liquids
journal, January 2017
- Pierson, Stephen A.; Nacham, Omprakash; Clark, Kevin D.
- New Journal of Chemistry, Vol. 41, Issue 13
Structure and magnetic behavior of transition metal based ionic liquids
journal, January 2008
- Del Sesto, Rico E.; McCleskey, T. Mark; Burrell, Anthony K.
- Chem. Commun., Issue 4
Faster dispersive liquid-liquid microextraction methods using magnetic ionic liquids as solvents
journal, September 2016
- Yu, Honglian; Merib, Josias; Anderson, Jared L.
- Journal of Chromatography A, Vol. 1463
Dicationic ionic liquid thermal decomposition pathways
journal, January 2018
- Patil, Rahul A.; Talebi, Mohsen; Berthod, Alain
- Analytical and Bioanalytical Chemistry, Vol. 410, Issue 19
Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography
journal, March 2015
- Zhang, Cheng; Ingram, Isaiah C.; Hantao, Leandro W.
- Journal of Chromatography A, Vol. 1386
Headspace single drop microextraction versus dispersive liquid-liquid microextraction using magnetic ionic liquid extraction solvents
journal, May 2017
- An, Jiwoo; Rahn, Kira L.; Anderson, Jared L.
- Talanta, Vol. 167
Copper(II), cobalt(II), nickel(II) and zinc(II) complexes of Schiff base derived from benzil-2,4-dinitrophenylhydrazone with aniline
journal, July 2004
- Raman, N.; Ravichandran, S.; Thangaraja, C.
- Journal of Chemical Sciences, Vol. 116, Issue 4
Anhydrous Praseodymium Salts in the Ionic Liquid [bmpyr][Tf 2 N]: Structural and Optical Properties of [bmpyr] 4 [PrI 6 ][Tf 2 N] and [bmyr] 2 [Pr(Tf 2 N) 5 ]
journal, December 2005
- Babai, Arash; Mudring, Anja-Verena
- Chemistry of Materials, Vol. 17, Issue 25
Metal-Containing Ionic Liquids as Efficient Catalysts for Hydroxymethylation in Water
journal, July 2008
- Bica, Katharina; Gaertner, Peter
- European Journal of Organic Chemistry, Vol. 2008, Issue 20
Evaluating the solvation properties of metal-containing ionic liquids using the solvation parameter model
journal, December 2017
- Nan, He; Peterson, Liese; Anderson, Jared L.
- Analytical and Bioanalytical Chemistry, Vol. 410, Issue 19
Polarity study of some 1-alkyl-3-methylimidazolium ambient-temperature ionic liquids with the solvatochromic dye, Nile Red
journal, January 2000
- Carmichael, Adrian J.; Seddon, Kenneth R.
- Journal of Physical Organic Chemistry, Vol. 13, Issue 10
Highly efficient extraction of phenolic compounds by use of magnetic room temperature ionic liquids for environmental remediation
journal, September 2011
- Deng, Ning; Li, Min; Zhao, Lijie
- Journal of Hazardous Materials, Vol. 192, Issue 3
Complex Ions. IX. Magnetic Susceptibilities of Nickel and Cobalt Complex Ions from 0 to 80°
journal, July 1949
- Field, Frank H.; Vosburgh, W. C.
- Journal of the American Chemical Society, Vol. 71, Issue 7
A demonstration of crystal-field effects in octahedral complexes
journal, October 1996
- Koubek, Edward; Elert, Mark
- Journal of Chemical Education, Vol. 73, Issue 10
Discovery of a Magnetic Ionic Liquid [bmim]FeCl 4
journal, December 2004
- Hayashi, Satoshi; Hamaguchi, Hiro-o
- Chemistry Letters, Vol. 33, Issue 12
Electrochromic and magnetic ionic liquids
journal, January 2011
- Branco, Aida; Branco, Luís C.; Pina, Fernando
- Chem. Commun., Vol. 47, Issue 8
Preparation and evaluation of cellulose-dissolving magnetic ionic liquid
journal, June 2013
- Muraoka, Jin; Kamiya, Noriho; Ito, Yuji
- Journal of Molecular Liquids, Vol. 182
Magnetic ionic liquids in analytical chemistry: A review
journal, August 2016
- Clark, Kevin D.; Nacham, Omprakash; Purslow, Jeffrey A.
- Analytica Chimica Acta, Vol. 934
Solvatochromic Dyes as Solvent Polarity Indicators
journal, December 1994
- Reichardt, Christian
- Chemical Reviews, Vol. 94, Issue 8
Application of Iron-Containing Magnetic Ionic Liquids in Extraction Process of Coal Direct Liquefaction Residues
journal, February 2012
- Wang, Jieli; Yao, Hongwei; Nie, Yi
- Industrial & Engineering Chemistry Research, Vol. 51, Issue 9
Metal isotope effect on metal-ligand vibrations. IV. Metal complexes of acetylacetone
journal, July 1970
- Nakamoto, Kazuo.; Udovich, Carl.; Takemoto, James.
- Journal of the American Chemical Society, Vol. 92, Issue 13
Hydrophobic ionic liquids with strongly coordinating anions
journal, January 2010
- Mehdi, Hasan; Binnemans, Koen; Van Hecke, Kristof
- Chem. Commun., Vol. 46, Issue 2
Using a Combination of Experimental and Computational Methods To Explore the Impact of Metal Identity and Ligand Field Strength on the Electronic Structure of Metal Ions
journal, September 2011
- Pernicone, Naomi C.; Geri, Jacob B.; York, John T.
- Journal of Chemical Education, Vol. 88, Issue 9
Discovery of a Magnetic Ionic Liquid [bmim]FeCl4.
journal, May 2005
- Hayashi, Satoshi; Hamaguchi, Hiro-o
- ChemInform, Vol. 36, Issue 18
Works referencing / citing this record:
Trigonal-Prismatic vs. Octahedral Geometry for MnII Complexes with Innocent Didentate Ligands: A Subtle Difference as Shown by XRD and DFT on [Mn(acac)2(bpy)]
journal, June 2005
- van Gorkum, Remy; Buda, Francesco; Kooijman, Huub
- European Journal of Inorganic Chemistry, Vol. 2005, Issue 11
Metal-Containing Ionic Liquids as Efficient Catalysts for Hydroxymethylation in Water
journal, July 2008
- Bica, Katharina; Gaertner, Peter
- European Journal of Organic Chemistry, Vol. 2008, Issue 20
Synthesis and characterization of Magnetic Ionic Liquids (MILs) for CO 2 separation
journal, May 2014
- Santos, Esther; Albo, Jonathan; Rosatella, Andreia
- Journal of Chemical Technology & Biotechnology, Vol. 89, Issue 6
Physicochemical characterization of paramagnetic ionic liquids 1-vinyl-3-alkylimidazolium tetrahalogenidoferrate(III) [VRIM][FeCl m Br 4 − m ] : PHYSICOCHEMICAL CHARACTERIZATION OF PARAMAGNETIC IONIC LIQUIDS
journal, February 2014
- Tang, Yimei; Hu, Xiaoling; Guan, Ping
- Journal of Physical Organic Chemistry, Vol. 27, Issue 6
Evaluating the solvation properties of metal-containing ionic liquids using the solvation parameter model
journal, December 2017
- Nan, He; Peterson, Liese; Anderson, Jared L.
- Analytical and Bioanalytical Chemistry, Vol. 410, Issue 19
Dicationic ionic liquid thermal decomposition pathways
journal, January 2018
- Patil, Rahul A.; Talebi, Mohsen; Berthod, Alain
- Analytical and Bioanalytical Chemistry, Vol. 410, Issue 19
Magnetic ionic liquids in analytical chemistry: A review
journal, August 2016
- Clark, Kevin D.; Nacham, Omprakash; Purslow, Jeffrey A.
- Analytica Chimica Acta, Vol. 934
Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography
journal, March 2015
- Zhang, Cheng; Ingram, Isaiah C.; Hantao, Leandro W.
- Journal of Chromatography A, Vol. 1386
Faster dispersive liquid-liquid microextraction methods using magnetic ionic liquids as solvents
journal, September 2016
- Yu, Honglian; Merib, Josias; Anderson, Jared L.
- Journal of Chromatography A, Vol. 1463
Thermophysical and magnetic studies of two paramagnetic liquid salts: [C4mim][FeCl4] and [P66614][FeCl4]
journal, July 2013
- Cruz, M. M.; Borges, R. P.; Godinho, M.
- Fluid Phase Equilibria, Vol. 350
Solubility and phase behavior of binary systems containing salts based on transitional metals
journal, August 2013
- Zakrzewska, Małgorzata E.; Paninho, Ana B.; Môlho, Marta F.
- The Journal of Chemical Thermodynamics, Vol. 63
Highly efficient extraction of phenolic compounds by use of magnetic room temperature ionic liquids for environmental remediation
journal, September 2011
- Deng, Ning; Li, Min; Zhao, Lijie
- Journal of Hazardous Materials, Vol. 192, Issue 3
Tetraalkylphosphonium-based ionic liquids
journal, May 2005
- Del Sesto, Rico E.; Corley, Cynthia; Robertson, Al
- Journal of Organometallic Chemistry, Vol. 690, Issue 10, p. 2536-2542
Preparation and evaluation of cellulose-dissolving magnetic ionic liquid
journal, June 2013
- Muraoka, Jin; Kamiya, Noriho; Ito, Yuji
- Journal of Molecular Liquids, Vol. 182
Headspace single drop microextraction versus dispersive liquid-liquid microextraction using magnetic ionic liquid extraction solvents
journal, May 2017
- An, Jiwoo; Rahn, Kira L.; Anderson, Jared L.
- Talanta, Vol. 167
Paramagnetic Ionic Liquids for Measurements of Density Using Magnetic Levitation
journal, August 2013
- Bwambok, David K.; Thuo, Martin M.; Atkinson, Manza B. J.
- Analytical Chemistry, Vol. 85, Issue 17
Trigonal Tricationic Ionic Liquids: A Generation of Gas Chromatographic Stationary Phases
journal, January 2009
- Payagala, Tharanga; Zhang, Ying; Wanigasekara, Eranda
- Analytical Chemistry, Vol. 81, Issue 1
Anhydrous Praseodymium Salts in the Ionic Liquid [bmpyr][Tf 2 N]: Structural and Optical Properties of [bmpyr] 4 [PrI 6 ][Tf 2 N] and [bmyr] 2 [Pr(Tf 2 N) 5 ]
journal, December 2005
- Babai, Arash; Mudring, Anja-Verena
- Chemistry of Materials, Vol. 17, Issue 25
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
Solvatochromic Dyes as Solvent Polarity Indicators
journal, December 1994
- Reichardt, Christian
- Chemical Reviews, Vol. 94, Issue 8
Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2
journal, May 2011
- Hallett, Jason P.; Welton, Tom
- Chemical Reviews, Vol. 111, Issue 5
A demonstration of crystal-field effects in octahedral complexes
journal, October 1996
- Koubek, Edward; Elert, Mark
- Journal of Chemical Education, Vol. 73, Issue 10
Using a Combination of Experimental and Computational Methods To Explore the Impact of Metal Identity and Ligand Field Strength on the Electronic Structure of Metal Ions
journal, September 2011
- Pernicone, Naomi C.; Geri, Jacob B.; York, John T.
- Journal of Chemical Education, Vol. 88, Issue 9
Extractive Desulfurization Using Fe-Containing Ionic Liquids
journal, May 2008
- Ko, Nan Hee; Lee, Je Seung; Huh, Eun Soo
- Energy & Fuels, Vol. 22, Issue 3
Application of Iron-Containing Magnetic Ionic Liquids in Extraction Process of Coal Direct Liquefaction Residues
journal, February 2012
- Wang, Jieli; Yao, Hongwei; Nie, Yi
- Industrial & Engineering Chemistry Research, Vol. 51, Issue 9
Metal isotope effect on metal-ligand vibrations. IV. Metal complexes of acetylacetone
journal, July 1970
- Nakamoto, Kazuo.; Udovich, Carl.; Takemoto, James.
- Journal of the American Chemical Society, Vol. 92, Issue 13
Complex Ions. IX. Magnetic Susceptibilities of Nickel and Cobalt Complex Ions from 0 to 80°
journal, July 1949
- Field, Frank H.; Vosburgh, W. C.
- Journal of the American Chemical Society, Vol. 71, Issue 7
Influence of structural variations in 1-alkyl-3-methylimidazolium cation and tetrahalogenoferrate(iii) anion on the physical properties of the paramagnetic ionic liquids
journal, January 2006
- Yoshida, Yukihiro; Saito, Gunzi
- Journal of Materials Chemistry, Vol. 16, Issue 13
Ionic liquids with metal chelate anions
journal, January 2012
- Zhang, Pengfei; Gong, Yutong; Lv, Yiqi
- Chemical Communications, Vol. 48, Issue 17
Sonochemical formation of iron oxide nanoparticles in ionic liquids for magnetic liquid marble
journal, January 2012
- Zhang, Shiguo; Zhang, Yan; Wang, Ying
- Physical Chemistry Chemical Physics, Vol. 14, Issue 15
Dication magnetic ionic liquids with tuneable heteroanions
journal, January 2013
- Brown, Paul; Butts, Craig P.; Eastoe, Julian
- Chemical Communications, Vol. 49, Issue 27
Discovery of a Magnetic Ionic Liquid [bmim]FeCl 4
journal, December 2004
- Hayashi, Satoshi; Hamaguchi, Hiro-o
- Chemistry Letters, Vol. 33, Issue 12
Metallocenium Ionic Liquids
journal, June 2010
- Inagaki, Takashi; Mochida, Tomoyuki
- Chemistry Letters, Vol. 39, Issue 6