Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water

Li, Ping; Damron, Josh; Bryantsev, Vyacheslav; Johnson, Katie; Stamberga, Diana; Mahurin, Shannon Mark; Popovs, Ilja; Jansone-Popova, Santa

doi:10.1021/acsanm.1c02845

Title: Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water

Abstract

Chromium- and arsenic-based oxoanions are among the major highly toxic and carcinogenic inorganic pollutants present in groundwater, demanding fast and selective sequestration. Efficient capturing and removal of these highly mobile oxometallates at neutral pH presents a great challenge in groundwater cleanup. In this report, a series of guanidinium-based ionic organic covalent nanosheets (iCONs) with varying hydrogen bonding, steric, and electronic properties was studied to examine the structure–activity relationship in the adsorption and removal of chromium- and arsenic-based oxoanions in water. Structural modulations in iCONs were found to alter the guanidinium acidity, thus regulating the oxoanion uptake limits via ion exchange. The hydrogen bonding, steric, and electrostatic interactions at/near the guanidinium-based anion binding site in iCONs exerted heavy influences on the uptake efficiency and selectivity of arsenate but not on those of chromate. Further analyses revealed that the parallel bidentate hydrogen bonding interactions play a key role in the weak binding of arsenate to the protonated/positively charged guanidine motifs, whereas the strong ion–ion interactions between chromate and guanidinium appear to be more tolerant to the geometric and structural perturbation.

Authors:

^[1];

^[1]

Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Publication Date:: Thu Nov 18 00:00:00 EST 2021

Research Org.:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

OSTI Identifier:: 1846532

Grant/Contract Number:: AC05-00OR22725; ERKCC08; ERKCT08

Resource Type:: Accepted Manuscript

Journal Name:: ACS Applied Nano Materials

Additional Journal Information:: Journal Volume: 4; Journal Issue: 12; Journal ID: ISSN 2574-0970

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 36 MATERIALS SCIENCE; guanidinium; ion exchange; nanosheet; chromium; arsenic; oxoanion sequestration

Citation Formats


                    Li, Ping, Damron, Josh, Bryantsev, Vyacheslav, Johnson, Katie, Stamberga, Diana, Mahurin, Shannon Mark, Popovs, Ilja, and Jansone-Popova, Santa. Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water.  United States: N. p., 2021. 
Web.  doi:10.1021/acsanm.1c02845.

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                    Li, Ping, Damron, Josh, Bryantsev, Vyacheslav, Johnson, Katie, Stamberga, Diana, Mahurin, Shannon Mark, Popovs, Ilja, & Jansone-Popova, Santa. Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water.  United States.  https://doi.org/10.1021/acsanm.1c02845

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                    Li, Ping, Damron, Josh, Bryantsev, Vyacheslav, Johnson, Katie, Stamberga, Diana, Mahurin, Shannon Mark, Popovs, Ilja, and Jansone-Popova, Santa. Thu .  
"Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water".  United States.  https://doi.org/10.1021/acsanm.1c02845.  https://www.osti.gov/servlets/purl/1846532.

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@article{osti_1846532,

  title        = {Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water},

  author       = {Li, Ping and Damron, Josh and Bryantsev, Vyacheslav and Johnson, Katie and Stamberga, Diana and Mahurin, Shannon Mark and Popovs, Ilja and Jansone-Popova, Santa},

  abstractNote = {Chromium- and arsenic-based oxoanions are among the major highly toxic and carcinogenic inorganic pollutants present in groundwater, demanding fast and selective sequestration. Efficient capturing and removal of these highly mobile oxometallates at neutral pH presents a great challenge in groundwater cleanup. In this report, a series of guanidinium-based ionic organic covalent nanosheets (iCONs) with varying hydrogen bonding, steric, and electronic properties was studied to examine the structure–activity relationship in the adsorption and removal of chromium- and arsenic-based oxoanions in water. Structural modulations in iCONs were found to alter the guanidinium acidity, thus regulating the oxoanion uptake limits via ion exchange. The hydrogen bonding, steric, and electrostatic interactions at/near the guanidinium-based anion binding site in iCONs exerted heavy influences on the uptake efficiency and selectivity of arsenate but not on those of chromate. Further analyses revealed that the parallel bidentate hydrogen bonding interactions play a key role in the weak binding of arsenate to the protonated/positively charged guanidine motifs, whereas the strong ion–ion interactions between chromate and guanidinium appear to be more tolerant to the geometric and structural perturbation.},

  doi          = {10.1021/acsanm.1c02845},

  journal      = {ACS Applied Nano Materials},

  number       = 12,

  volume       = 4,

  place        = {United States},

  year         = {Thu Nov 18 00:00:00 EST 2021},

  month        = {Thu Nov 18 00:00:00 EST 2021}

}

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Title: Guanidinium-Based Ionic Covalent-Organic Nanosheets for Sequestration of Cr(VI) and As(V) Oxoanions in Water

Abstract

Citation Formats

3D Metallo-organic coordination assembly-based anion-enriched supramolecular material for fast and efficient removal of Cr2O72− journal, March 2021

Water-stable metal-organic frameworks for aqueous removal of heavy metals and radionuclides: A review journal, October 2018

Arsenic Removal from Natural Waters by Adsorption or Ion Exchange: An Environmental Sustainability Assessment journal, February 2014

Structural Approaches to Control Interlayer Interactions in 2D Covalent Organic Frameworks journal, August 2020

Chemically stable ionic viologen-organic network: an efficient scavenger of toxic oxo-anions from water journal, January 2018

Cr(VI) removal via anion exchange on a silver-triazolate MOF journal, January 2017

Arsenic removal from water/wastewater using adsorbents—A critical review journal, April 2007

Computationally-Guided Synthetic Control over Pore Size in Isostructural Porous Organic Cages journal, June 2017

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions journal, May 2009

Redox-Triggered Buoyancy and Size Modulation of a Dynamic Covalent Gel journal, April 2019

Exploring ion-ion preferences through structure-property correlations: amino acid-derived, bis(guanidinium) disiloxane salts journal, January 2020

Metal-organic frameworks: Challenges and opportunities for ion-exchange/sorption applications journal, May 2017

Trace Cr(VI) Removal: Evidence of Redox-Active Ion Exchange by a Weak-Base Anion Exchanger journal, November 2020

Metal–organic framework technologies for water remediation: towards a sustainable ecosystem journal, January 2018

Guanidinium-Based Ionic Covalent Organic Framework for Rapid and Selective Removal of Toxic Cr(VI) Oxoanions from Water journal, October 2018

Exfoliation of Covalent Organic Frameworks into Few-Layer Redox-Active Nanosheets as Cathode Materials for Lithium-Ion Batteries journal, March 2017

Sorption isotherms: A review on physical bases, modeling and measurement journal, February 2007

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals journal, July 2007

Evaluating of arsenic(V) removal from water by weak-base anion exchange adsorbents journal, May 2012

A Versatile Cationic Organic Network Adsorbent for the Highly Efficient Removal of Diverse Water Contaminants journal, April 2021

Electrochemical reduction of Cr( vi ) in water: lessons learned from fundamental studies and applications journal, January 2021

Bifunctional Ionic Covalent Organic Networks for Enhanced Simultaneous Removal of Chromium(VI) and Arsenic(V) Oxoanions via Synergetic Ion Exchange and Redox Process journal, October 2021

Sources and toxicity of hexavalent chromium journal, May 2011

Synthesis of N -Methylimidazolium Functionalized Strongly Basic Anion Exchange Resins for Adsorption of Cr(VI) journal, February 2009

Multifunctional ionic porous frameworks for CO 2 conversion and combating microbes journal, January 2020

Health Effects of Arsenic and Chromium in Drinking Water: Recent Human Findings journal, April 2009

Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters journal, August 2015

A Water‐Stable Ionic MOF for the Selective Capture of Toxic Oxoanions of Se VI and As V and Crystallographic Insight into the Ion‐Exchange Mechanism journal, March 2020

High-performance adsorption of chromate by hydrazone-linked guanidinium-based ionic covalent organic frameworks: Selective ion exchange journal, November 2021

A Computational Approach to Predicting Ligand Selectivity for the Size-Based Separation of Trivalent Lanthanides: A Computational Approach to Predicting Ligand Selectivity for the Size-Based Separation of Trivalent Lanthanides journal, June 2016

Cationic Amorphous Metal–Organic Cage-Based Materials for the Removal of Oxo-Anions from Water journal, August 2019

Predicting Hydrogen-Bond Strengths from Acid−Base Molecular Properties. The p K a Slide Rule: Toward the Solution of a Long-Lasting Problem journal, January 2009

A Water-Stable Cationic Metal-Organic Framework as a Dual Adsorbent of Oxoanion Pollutants journal, February 2016

Aquatic arsenic: Toxicity, speciation, transformations, and remediation journal, May 2009

Covalent organic framework membranes through a mixed-dimensional assembly for molecular separations journal, May 2019

Arsenic and fluoride contaminated groundwaters: A review of current technologies for contaminants removal journal, October 2015

A review of chemical, electrochemical and biological methods for aqueous Cr(VI) reduction journal, July 2012

Cationic Covalent Organic Nanosheets for Rapid and Selective Capture of Perrhenate: An Analogue of Radioactive Pertechnetate from Aqueous Solution journal, April 2019

Hydration of Oxometallate Ions in Aqueous Solution journal, May 2020

A Water-Stable Cationic Metal–Organic Framework with Hydrophobic Pore Surfaces as an Efficient Scavenger of Oxo-Anion Pollutants from Water journal, August 2020

Proton-Triggered Fluorescence Switching in Self-Exfoliated Ionic Covalent Organic Nanosheets for Applications in Selective Detection of Anions journal, February 2020

Performance of SM6, SM8, and SMD on the SAMPL1 Test Set for the Prediction of Small-Molecule Solvation Free Energies journal, April 2009

Ultralow Surface Tension Solvents Enable Facile COF Activation with Reduced Pore Collapse journal, June 2020

Cationic Covalent Organic Framework Nanosheets for Fast Li-Ion Conduction journal, January 2018

Covalent organic framework nanosheets: preparation, properties and applications journal, January 2020

Rapid Synthesis of High Surface Area Imine‐Linked 2D Covalent Organic Frameworks by Avoiding Pore Collapse During Isolation journal, November 2019

Covalent organic framework EB-COF:Br as adsorbent for phosphorus (V) or arsenic (V) removal from nearly neutral waters journal, August 2020

Zwitterion π–conjugated network polymer based on guanidinium and β-ketoenol as a heterogeneous organo-catalyst for chemical fixation of CO 2 into cyclic carbonates journal, November 2019

Technologies for Arsenic Removal from Water: Current Status and Future Perspectives journal, December 2015

Self-Exfoliated Guanidinium-Based Ionic Covalent Organic Nanosheets (iCONs) journal, February 2016

Solving the COF trilemma: towards crystalline, stable and functional covalent organic frameworks journal, January 2020

A simple empirical model describing the thermodynamics of hydration of ions of widely varying charges, sizes, and shapes journal, August 1994

Chromate separation by selective crystallization journal, July 2020

Global Water Pollution and Human Health journal, November 2010

Selective removal of the heavy metal ions from waters and industrial wastewaters by ion-exchange method journal, July 2004

Metal–organic frameworks for applications in remediation of oxyanion/cation-contaminated water journal, January 2015

2D-Covalent Organic Frameworks with Interlayer Hydrogen Bonding Oriented through Designed Nonplanarity journal, July 2020

Covalent organic frameworks for separation applications journal, January 2020

Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994) journal, January 1994

Global threat of arsenic in groundwater journal, May 2020

3D Metallo-organic coordination assembly-based anion-enriched supramolecular material for fast and efficient removal of Cr2O72−
journal, March 2021

Water-stable metal-organic frameworks for aqueous removal of heavy metals and radionuclides: A review
journal, October 2018

Arsenic Removal from Natural Waters by Adsorption or Ion Exchange: An Environmental Sustainability Assessment
journal, February 2014

Structural Approaches to Control Interlayer Interactions in 2D Covalent Organic Frameworks
journal, August 2020

Chemically stable ionic viologen-organic network: an efficient scavenger of toxic oxo-anions from water
journal, January 2018

Cr(VI) removal via anion exchange on a silver-triazolate MOF
journal, January 2017

Arsenic removal from water/wastewater using adsorbents—A critical review
journal, April 2007

Computationally-Guided Synthetic Control over Pore Size in Isostructural Porous Organic Cages
journal, June 2017

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions
journal, May 2009

Redox-Triggered Buoyancy and Size Modulation of a Dynamic Covalent Gel
journal, April 2019

Exploring ion-ion preferences through structure-property correlations: amino acid-derived, bis(guanidinium) disiloxane salts
journal, January 2020

Metal-organic frameworks: Challenges and opportunities for ion-exchange/sorption applications
journal, May 2017

Trace Cr(VI) Removal: Evidence of Redox-Active Ion Exchange by a Weak-Base Anion Exchanger
journal, November 2020

Metal–organic framework technologies for water remediation: towards a sustainable ecosystem
journal, January 2018

Guanidinium-Based Ionic Covalent Organic Framework for Rapid and Selective Removal of Toxic Cr(VI) Oxoanions from Water
journal, October 2018

Exfoliation of Covalent Organic Frameworks into Few-Layer Redox-Active Nanosheets as Cathode Materials for Lithium-Ion Batteries
journal, March 2017

Sorption isotherms: A review on physical bases, modeling and measurement
journal, February 2007

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007

Evaluating of arsenic(V) removal from water by weak-base anion exchange adsorbents
journal, May 2012

A Versatile Cationic Organic Network Adsorbent for the Highly Efficient Removal of Diverse Water Contaminants
journal, April 2021

Electrochemical reduction of Cr( vi ) in water: lessons learned from fundamental studies and applications
journal, January 2021

Bifunctional Ionic Covalent Organic Networks for Enhanced Simultaneous Removal of Chromium(VI) and Arsenic(V) Oxoanions via Synergetic Ion Exchange and Redox Process
journal, October 2021

Sources and toxicity of hexavalent chromium
journal, May 2011

Synthesis of N -Methylimidazolium Functionalized Strongly Basic Anion Exchange Resins for Adsorption of Cr(VI)
journal, February 2009

Multifunctional ionic porous frameworks for CO ₂ conversion and combating microbes
journal, January 2020

Health Effects of Arsenic and Chromium in Drinking Water: Recent Human Findings
journal, April 2009

Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
journal, August 2015

A Water‐Stable Ionic MOF for the Selective Capture of Toxic Oxoanions of Se ^VI and As ^V and Crystallographic Insight into the Ion‐Exchange Mechanism
journal, March 2020

High-performance adsorption of chromate by hydrazone-linked guanidinium-based ionic covalent organic frameworks: Selective ion exchange
journal, November 2021

A Computational Approach to Predicting Ligand Selectivity for the Size-Based Separation of Trivalent Lanthanides: A Computational Approach to Predicting Ligand Selectivity for the Size-Based Separation of Trivalent Lanthanides
journal, June 2016

Cationic Amorphous Metal–Organic Cage-Based Materials for the Removal of Oxo-Anions from Water
journal, August 2019

Predicting Hydrogen-Bond Strengths from Acid−Base Molecular Properties. The p K _a Slide Rule: Toward the Solution of a Long-Lasting Problem
journal, January 2009

A Water-Stable Cationic Metal-Organic Framework as a Dual Adsorbent of Oxoanion Pollutants
journal, February 2016

Aquatic arsenic: Toxicity, speciation, transformations, and remediation
journal, May 2009

Covalent organic framework membranes through a mixed-dimensional assembly for molecular separations
journal, May 2019

Arsenic and fluoride contaminated groundwaters: A review of current technologies for contaminants removal
journal, October 2015

A review of chemical, electrochemical and biological methods for aqueous Cr(VI) reduction
journal, July 2012

Cationic Covalent Organic Nanosheets for Rapid and Selective Capture of Perrhenate: An Analogue of Radioactive Pertechnetate from Aqueous Solution
journal, April 2019

Hydration of Oxometallate Ions in Aqueous Solution
journal, May 2020

A Water-Stable Cationic Metal–Organic Framework with Hydrophobic Pore Surfaces as an Efficient Scavenger of Oxo-Anion Pollutants from Water
journal, August 2020

Proton-Triggered Fluorescence Switching in Self-Exfoliated Ionic Covalent Organic Nanosheets for Applications in Selective Detection of Anions
journal, February 2020

Performance of SM6, SM8, and SMD on the SAMPL1 Test Set for the Prediction of Small-Molecule Solvation Free Energies
journal, April 2009

Ultralow Surface Tension Solvents Enable Facile COF Activation with Reduced Pore Collapse
journal, June 2020

Cationic Covalent Organic Framework Nanosheets for Fast Li-Ion Conduction
journal, January 2018

Covalent organic framework nanosheets: preparation, properties and applications
journal, January 2020

Rapid Synthesis of High Surface Area Imine‐Linked 2D Covalent Organic Frameworks by Avoiding Pore Collapse During Isolation
journal, November 2019

Covalent organic framework EB-COF:Br as adsorbent for phosphorus (V) or arsenic (V) removal from nearly neutral waters
journal, August 2020

Zwitterion π–conjugated network polymer based on guanidinium and β-ketoenol as a heterogeneous organo-catalyst for chemical fixation of CO ₂ into cyclic carbonates
journal, November 2019

Technologies for Arsenic Removal from Water: Current Status and Future Perspectives
journal, December 2015

Self-Exfoliated Guanidinium-Based Ionic Covalent Organic Nanosheets (iCONs)
journal, February 2016

Solving the COF trilemma: towards crystalline, stable and functional covalent organic frameworks
journal, January 2020

A simple empirical model describing the thermodynamics of hydration of ions of widely varying charges, sizes, and shapes
journal, August 1994

Chromate separation by selective crystallization
journal, July 2020

Global Water Pollution and Human Health
journal, November 2010

Selective removal of the heavy metal ions from waters and industrial wastewaters by ion-exchange method
journal, July 2004

Metal–organic frameworks for applications in remediation of oxyanion/cation-contaminated water
journal, January 2015

2D-Covalent Organic Frameworks with Interlayer Hydrogen Bonding Oriented through Designed Nonplanarity
journal, July 2020

Covalent organic frameworks for separation applications
journal, January 2020

Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)
journal, January 1994

Global threat of arsenic in groundwater
journal, May 2020