Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor
Abstract
Here, we report a novel di(imino)guanidinium anion extractant with unparalleled selectivity for sulfate in a liquid–liquid separation system. In addition to a 4.4 order-of-magnitude enhancement in affinity compared to a standard benchmark, our alkylated di(imino)guanidinium receptor is economically synthesized and features good compatibility with application-relevant aliphatic solvents. Small-angle X-ray scattering results reveal the formation of reverse-micelles, which together with the significant organic-phase water content challenge traditional notions of selectivity in extraction of superhydrophilic anions.
- Authors:
-
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); The Univ. of Tennessee, Knoxville, TN (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); The Univ. of Texas at Austin, Austin, TX (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1468178
- Alternate Identifier(s):
- OSTI ID: 1465223
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ChemComm
- Additional Journal Information:
- Journal Volume: 54; Journal Issue: 72; Journal ID: ISSN 1359-7345
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Williams, Neil J., Seipp, Charles A., Garrabrant, Kathleen A., Custelcean, Radu, Holguin, Erick, Keum, Jong K., Ellis, Ross J., and Moyer, Bruce A. Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor. United States: N. p., 2018.
Web. doi:10.1039/c8cc05115a.
Williams, Neil J., Seipp, Charles A., Garrabrant, Kathleen A., Custelcean, Radu, Holguin, Erick, Keum, Jong K., Ellis, Ross J., & Moyer, Bruce A. Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor. United States. https://doi.org/10.1039/c8cc05115a
Williams, Neil J., Seipp, Charles A., Garrabrant, Kathleen A., Custelcean, Radu, Holguin, Erick, Keum, Jong K., Ellis, Ross J., and Moyer, Bruce A. Mon .
"Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor". United States. https://doi.org/10.1039/c8cc05115a. https://www.osti.gov/servlets/purl/1468178.
@article{osti_1468178,
title = {Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor},
author = {Williams, Neil J. and Seipp, Charles A. and Garrabrant, Kathleen A. and Custelcean, Radu and Holguin, Erick and Keum, Jong K. and Ellis, Ross J. and Moyer, Bruce A.},
abstractNote = {Here, we report a novel di(imino)guanidinium anion extractant with unparalleled selectivity for sulfate in a liquid–liquid separation system. In addition to a 4.4 order-of-magnitude enhancement in affinity compared to a standard benchmark, our alkylated di(imino)guanidinium receptor is economically synthesized and features good compatibility with application-relevant aliphatic solvents. Small-angle X-ray scattering results reveal the formation of reverse-micelles, which together with the significant organic-phase water content challenge traditional notions of selectivity in extraction of superhydrophilic anions.},
doi = {10.1039/c8cc05115a},
journal = {ChemComm},
number = 72,
volume = 54,
place = {United States},
year = {Mon Aug 20 00:00:00 EDT 2018},
month = {Mon Aug 20 00:00:00 EDT 2018}
}
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Works referenced in this record:
Selectivity Principles in Anion Separation by Crystallization of Hydrogen-Bonding Capsules
journal, May 2010
- Custelcean, Radu; Bock, Aurelien; Moyer, Bruce A.
- Journal of the American Chemical Society, Vol. 132, Issue 20
Structural Design Criteria for Anion Hosts: Strategies for Achieving Anion Shape Recognition through the Complementary Placement of Urea Donor Groups
journal, February 2005
- Hay, Benjamin P.; Firman, Timothy K.; Moyer, Bruce A.
- Journal of the American Chemical Society, Vol. 127, Issue 6
Binding Hydrated Anions with Hydrophobic Pockets
journal, December 2015
- Sokkalingam, Punidha; Shraberg, Joshua; Rick, Steven W.
- Journal of the American Chemical Society, Vol. 138, Issue 1
A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds
journal, January 2015
- Seipp, Charles A.; Williams, Neil J.; Bryantsev, Vyacheslav S.
- RSC Advances, Vol. 5, Issue 130
Synthetic transporters for sulfate: a new method for the direct detection of lipid bilayer sulfate transport
journal, January 2014
- Busschaert, Nathalie; Karagiannidis, Louise E.; Wenzel, Marco
- Chemical Science, Vol. 5, Issue 3
Reverse osmosis desalination: Water sources, technology, and today's challenges
journal, May 2009
- Greenlee, Lauren F.; Lawler, Desmond F.; Freeman, Benny D.
- Water Research, Vol. 43, Issue 9
Evaluation of small-angle scattering data of charged particles using the generalized indirect Fourier transformation technique
journal, December 2000
- Fritz, G.; Bergmann, A.; Glatter, O.
- The Journal of Chemical Physics, Vol. 113, Issue 21
Anion Separation with Metal–Organic Frameworks
journal, April 2007
- Custelcean, Radu; Moyer, Bruce A.
- European Journal of Inorganic Chemistry, Vol. 2007, Issue 10
A Case for Molecular Recognition in Nuclear Separations: Sulfate Separation from Nuclear Wastes
journal, June 2012
- Moyer, Bruce A.; Custelcean, Radu; Hay, Benjamin P.
- Inorganic Chemistry, Vol. 52, Issue 7
Anion-receptor molecules: Synthesis of a chiral and functionalized binding subunit, a bicyclic guanidinium group derived from L - or D - asparagine
journal, June 1988
- Echavarren, Antonio; Galán, Amalia; de Mendoza, Javier
- Helvetica Chimica Acta, Vol. 71, Issue 4
Phosphorus resources, their depletion and conservation, a review
journal, December 2014
- Reijnders, L.
- Resources, Conservation and Recycling, Vol. 93
Crystallographic Evidence for Oxygen Acceptor Directionality in Oxyanion Hydrogen Bonds
journal, January 2002
- Hay, Benjamin P.; Dixon, David A.; Bryan, Jeffrey C.
- Journal of the American Chemical Society, Vol. 124, Issue 2
Sulfate scale problems in oil fields water injection operations
journal, November 2006
- Bader, M. S. H.
- Desalination, Vol. 201, Issue 1-3
Overview of the strategic approaches for the solid-state recognition of hydrated anions
journal, January 2017
- Hoque, Md. Najbul; Das, Gopal
- CrystEngComm, Vol. 19, Issue 10
CO 2 Capture from Ambient Air by Crystallization with a Guanidine Sorbent
journal, December 2016
- Seipp, Charles A.; Williams, Neil J.; Kidder, Michelle K.
- Angewandte Chemie International Edition, Vol. 56, Issue 4
Künstliche molekulare Anion-Wirte. Die Synthese eines chiralen bicyclischen Guanidinium-Salzes als funktionalisierte Ankergruppe für Oxo-Anionen
journal, April 1990
- Gleich, Alexander; Schmidtcher, Franz P.; Scheuplein, Stefan W.
- Chemische Berichte, Vol. 123, Issue 4
Aqueous Sulfate Separation by Sequestration of [(SO 4 ) 2 (H 2 O) 4 ] 4− Clusters within Highly Insoluble Imine-Linked Bis-Guanidinium Crystals
journal, December 2015
- Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
- Chemistry - A European Journal, Vol. 22, Issue 6
New Insights into the Anion Transport Selectivity and Mechanism of Tren-based Tris-(thio)ureas
journal, June 2018
- Jowett, Laura A.; Howe, Ethan N. W.; Wu, Xin
- Chemistry - A European Journal, Vol. 24, Issue 41
Structural studies of microemulsions stabilised by aerosol-OT
journal, July 1991
- Eastoe, Julian; Robinson, Brian H.; Steytler, David C.
- Advances in Colloid and Interface Science, Vol. 36
The interpretation of real-space information from small-angle scattering experiments
journal, April 1979
- Glatter, O.
- Journal of Applied Crystallography, Vol. 12, Issue 2
Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
journal, August 2015
- Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
- Angewandte Chemie International Edition, Vol. 54, Issue 36
Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
journal, August 2015
- Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
- Angewandte Chemie, Vol. 127, Issue 36
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journal, January 2019
- Huang, Zhe; Jia, Chuandong; Wu, Biao
- Chemical Communications, Vol. 55, Issue 12
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journal, January 2019
- Sukhbaatar, Tamir; Duvail, Magali; Dumas, Thomas
- Chemical Communications, Vol. 55, Issue 53
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journal, January 2019
- Jagleniec, Damian; Dobrzycki, Łukasz; Karbarz, Marcin
- Chemical Science, Vol. 10, Issue 41
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journal, January 2020
- Qin, Lei; Vervuurt, Sacha J. N.; Elmes, Robert B. P.
- Chemical Science, Vol. 11, Issue 1