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Title: 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:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [3]; ORCiD logo [3]; ORCiD logo [3]; ORCiD logo [3]; ORCiD logo [3]
  1. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); The Univ. of Tennessee, Knoxville, TN (United States)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); The Univ. of Texas at Austin, Austin, TX (United States)
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
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. doi: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. doi: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 = {2018},
month = {8}
}

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Cited by: 4 works
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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.
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New Insights into the Anion Transport Selectivity and Mechanism of Tren-based Tris-(thio)ureas
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Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
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    Works referencing / citing this record:

    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
    • DOI: 10.1002/anie.201506314

    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
    • DOI: 10.1002/anie.201610916

    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
    • DOI: 10.1002/cber.19901230442

    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
    • DOI: 10.1002/chem.201504651

    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
    • DOI: 10.1002/chem.201801463

    Anion Separation with Metal–Organic Frameworks
    journal, April 2007

    • Custelcean, Radu; Moyer, Bruce A.
    • European Journal of Inorganic Chemistry, Vol. 2007, Issue 10
    • DOI: 10.1002/ejic.200700018

    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
    • DOI: 10.1002/hlca.19880710402

    Sulfate scale problems in oil fields water injection operations
    journal, November 2006


    Phosphorus resources, their depletion and conservation, a review
    journal, December 2014


    Reverse osmosis desalination: Water sources, technology, and today's challenges
    journal, May 2009


    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
    • DOI: 10.1021/ic3016832

    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
    • DOI: 10.1021/ja0173775

    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
    • DOI: 10.1021/ja043995k

    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
    • DOI: 10.1021/ja101354r

    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
    • DOI: 10.1021/jacs.5b10937

    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
    • DOI: 10.1039/c3sc52006d

    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
    • DOI: 10.1063/1.1321770

    Selective binding of (thio)sulfate and phosphate in water by quaternary ammonium functionalized oligo-ureas
    journal, January 2019

    • Huang, Zhe; Jia, Chuandong; Wu, Biao
    • Chemical Communications, Vol. 55, Issue 12
    • DOI: 10.1039/c8cc09550g

    Probing the existence of uranyl trisulfate structures in the AMEX solvent extraction process
    journal, January 2019

    • Sukhbaatar, Tamir; Duvail, Magali; Dumas, Thomas
    • Chemical Communications, Vol. 55, Issue 53
    • DOI: 10.1039/c9cc02651g

    Ion-pair induced supramolecular assembly formation for selective extraction and sensing of potassium sulfate
    journal, January 2019

    • Jagleniec, Damian; Dobrzycki, Łukasz; Karbarz, Marcin
    • Chemical Science, Vol. 10, Issue 41
    • DOI: 10.1039/c9sc02923k