Nylon–MOF Composites through Postsynthetic Polymerization

Kalaj, Mark; Denny, Jr., Michael S.; Bentz, Kyle C.; Palomba, Joseph M.; Cohen, Seth M.

doi:10.1002/ange.201812655

Title: Nylon–MOF Composites through Postsynthetic Polymerization

Abstract

Abstract Hybridization of metal–organic frameworks (MOFs) and polymers into composites yields materials that display the exceptional properties of MOFs with the robustness of polymers. However, the realization of MOF–polymer composites requires efficient dispersion and interactions of MOF particles with polymer matrices, which remains a significant challenge. Herein, we report a simple, scalable, bench‐top approach to covalently tethered nylon–MOF polymer composite materials through an interfacial polymerization technique. The copolymerization of a modified UiO‐66‐NH ₂ MOF with a growing polyamide fiber (PA‐66) during an interfacial polymerization gave hybrid materials with up to around 29 weight percent MOF. The covalent hybrid material demonstrated nearly an order of magnitude higher catalytic activity for the breakdown of a chemical warfare simulant (dimethyl‐4‐nitrophenyl phosphate, DMNP) compared to MOFs that are non‐covalently, physically entrapped in nylon, thus highlighting the importance of MOF–polymer hybridization.

Authors:

Kalaj, Mark ^[1]; Denny, Jr., Michael S. ^[1]; Bentz, Kyle C. ^[1]; Palomba, Joseph M. ^[1];

^[1]

Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093 USA

Publication Date:: Mon Jan 21 00:00:00 EST 2019

Sponsoring Org.:: USDOE

OSTI Identifier:: 1491432

Grant/Contract Number:: FG02-08ER46519

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie

Additional Journal Information:: Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 8; Journal ID: ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Kalaj, Mark, Denny, Jr., Michael S., Bentz, Kyle C., Palomba, Joseph M., and Cohen, Seth M. Nylon–MOF Composites through Postsynthetic Polymerization.  Germany: N. p., 2019. 
Web.  doi:10.1002/ange.201812655.

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                    Kalaj, Mark, Denny, Jr., Michael S., Bentz, Kyle C., Palomba, Joseph M., & Cohen, Seth M. Nylon–MOF Composites through Postsynthetic Polymerization.  Germany.  https://doi.org/10.1002/ange.201812655

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                    Kalaj, Mark, Denny, Jr., Michael S., Bentz, Kyle C., Palomba, Joseph M., and Cohen, Seth M. Mon .  
"Nylon–MOF Composites through Postsynthetic Polymerization".  Germany.  https://doi.org/10.1002/ange.201812655.

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@article{osti_1491432,

  title        = {Nylon–MOF Composites through Postsynthetic Polymerization},

  author       = {Kalaj, Mark and Denny, Jr., Michael S. and Bentz, Kyle C. and Palomba, Joseph M. and Cohen, Seth M.},

  abstractNote = {Abstract Hybridization of metal–organic frameworks (MOFs) and polymers into composites yields materials that display the exceptional properties of MOFs with the robustness of polymers. However, the realization of MOF–polymer composites requires efficient dispersion and interactions of MOF particles with polymer matrices, which remains a significant challenge. Herein, we report a simple, scalable, bench‐top approach to covalently tethered nylon–MOF polymer composite materials through an interfacial polymerization technique. The copolymerization of a modified UiO‐66‐NH 2 MOF with a growing polyamide fiber (PA‐66) during an interfacial polymerization gave hybrid materials with up to around 29 weight percent MOF. The covalent hybrid material demonstrated nearly an order of magnitude higher catalytic activity for the breakdown of a chemical warfare simulant (dimethyl‐4‐nitrophenyl phosphate, DMNP) compared to MOFs that are non‐covalently, physically entrapped in nylon, thus highlighting the importance of MOF–polymer hybridization.},

  doi          = {10.1002/ange.201812655},

  journal      = {Angewandte Chemie},

  number       = 8,

  volume       = 131,

  place        = {Germany},

  year         = {Mon Jan 21 00:00:00 EST 2019},

  month        = {Mon Jan 21 00:00:00 EST 2019}

}

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Title: Nylon–MOF Composites through Postsynthetic Polymerization

Abstract

Citation Formats

Effective, Facile, and Selective Hydrolysis of the Chemical Warfare Agent VX Using Zr 6 -Based Metal–Organic Frameworks journal, October 2015

Isoreticular synthesis and modification of frameworks with the UiO-66 topology journal, January 2010

polyMOFs: A Class of Interconvertible Polymer-Metal-Organic-Framework Hybrid Materials journal, April 2015

Block co-polyMOFs: assembly of polymer–polyMOF hybrids via iterative exponential growth and “click” chemistry journal, January 2017

Mixed matrix membranes (MMMs) comprising organic polymers with dispersed inorganic fillers for gas separation journal, April 2007

Fabrication of a Substituted Imidazolate Material 1 (SIM-1) membrane using post synthetic modification (PSM) for pervaporation of water/ethanol mixtures journal, July 2015

Ultra-Fast Degradation of Chemical Warfare Agents Using MOF-Nanofiber Kebabs journal, October 2016

Metal–organic frameworks based membranes for liquid separation journal, January 2017

Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage journal, January 2002

Postsynthetic modification of metal–organic frameworks journal, January 2009

Hierarchical structure and porosity in UiO-66 polyMOFs journal, January 2017

In Situ Modification of Metal-Organic Frameworks in Mixed-Matrix Membranes journal, June 2015

Isoreticular expansion of polyMOFs achieves high surface area materials journal, January 2017

Metal-Organic Framework Membranes-High Potential, Bright Future? journal, February 2010

Ultra-Fast Degradation of Chemical Warfare Agents Using MOF-Nanofiber Kebabs journal, October 2016

Metall-organische Membranen: hohes Potenzial, große Zukunft? journal, February 2010

polyMOFs: A Class of Interconvertible Polymer-Metal-Organic-Framework Hybrid Materials journal, April 2015

Covalent immobilization of metal–organic frameworks onto the surface of nylon—a new approach to the functionalization and coloration of textiles journal, March 2016

Presence versus Proximity: The Role of Pendant Amines in the Catalytic Hydrolysis of a Nerve Agent Simulant journal, January 2018

Photoinduced Postsynthetic Polymerization of a Metal-Organic Framework toward a Flexible Stand-Alone Membrane journal, March 2015

MOFabric: Electrospun Nanofiber Mats from PVDF/UiO-66-NH 2 for Chemical Protection and Decontamination journal, April 2017

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Polymer–Metal–Organic Frameworks (polyMOFs) as Water Tolerant Materials for Selective Carbon Dioxide Separations journal, January 2016

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Cross-linking Zr-based metal–organic polyhedra via postsynthetic polymerization journal, January 2017

The Chemistry and Applications of Metal-Organic Frameworks journal, August 2013

In Situ Modification of Metal-Organic Frameworks in Mixed-Matrix Membranes journal, June 2015

Metal–organic frameworks for membrane-based separations journal, November 2016

Metal–organic frameworks for the removal of toxic industrial chemicals and chemical warfare agents journal, January 2017

Enhanced aging properties of HKUST-1 in hydrophobic mixed-matrix membranes for ammonia adsorption journal, January 2016

The Postsynthetic Renaissance in Porous Solids journal, February 2017

Presence versus Proximity: The Role of Pendant Amines in the Catalytic Hydrolysis of a Nerve Agent Simulant journal, January 2018

Photoinduced Postsynthetic Polymerization of a Metal-Organic Framework toward a Flexible Stand-Alone Membrane journal, March 2015

High-throughput screening of solid-state catalysts for nerve agent degradation journal, January 2018

Structure and crystallization behavior of Nylon 66/multi-walled carbon nanotube nanocomposites at low carbon nanotube contents journal, June 2007

Effective, Facile, and Selective Hydrolysis of the Chemical Warfare Agent VX Using Zr ₆ -Based Metal–Organic Frameworks
journal, October 2015

Isoreticular synthesis and modification of frameworks with the UiO-66 topology
journal, January 2010

polyMOFs: A Class of Interconvertible Polymer-Metal-Organic-Framework Hybrid Materials
journal, April 2015

Block co-polyMOFs: assembly of polymer–polyMOF hybrids via iterative exponential growth and “click” chemistry
journal, January 2017

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journal, April 2007

Fabrication of a Substituted Imidazolate Material 1 (SIM-1) membrane using post synthetic modification (PSM) for pervaporation of water/ethanol mixtures
journal, July 2015

Ultra-Fast Degradation of Chemical Warfare Agents Using MOF-Nanofiber Kebabs
journal, October 2016

Metal–organic frameworks based membranes for liquid separation
journal, January 2017

Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage
journal, January 2002

Postsynthetic modification of metal–organic frameworks
journal, January 2009

Hierarchical structure and porosity in UiO-66 polyMOFs
journal, January 2017

In Situ Modification of Metal-Organic Frameworks in Mixed-Matrix Membranes
journal, June 2015

Isoreticular expansion of polyMOFs achieves high surface area materials
journal, January 2017

Metal-Organic Framework Membranes-High Potential, Bright Future?
journal, February 2010

Ultra-Fast Degradation of Chemical Warfare Agents Using MOF-Nanofiber Kebabs
journal, October 2016

Metall-organische Membranen: hohes Potenzial, große Zukunft?
journal, February 2010

polyMOFs: A Class of Interconvertible Polymer-Metal-Organic-Framework Hybrid Materials
journal, April 2015

Covalent immobilization of metal–organic frameworks onto the surface of nylon—a new approach to the functionalization and coloration of textiles
journal, March 2016

Presence versus Proximity: The Role of Pendant Amines in the Catalytic Hydrolysis of a Nerve Agent Simulant
journal, January 2018

Photoinduced Postsynthetic Polymerization of a Metal-Organic Framework toward a Flexible Stand-Alone Membrane
journal, March 2015

MOFabric: Electrospun Nanofiber Mats from PVDF/UiO-66-NH ₂ for Chemical Protection and Decontamination
journal, April 2017

Catalytic degradation of chemical warfare agents and their simulants by metal-organic frameworks
journal, September 2017

Polymer–Metal–Organic Frameworks (polyMOFs) as Water Tolerant Materials for Selective Carbon Dioxide Separations
journal, January 2016

Post-Synthetic Polymerization of UiO-66-NH ₂ Nanoparticles and Polyurethane Oligomer toward Stand-Alone Membranes for Dye Removal and Separation
journal, June 2016

Selective gas adsorption and separation in metal–organic frameworks
journal, January 2009

Nanocomposites with Polymer Grafted Nanoparticles
journal, April 2013

UiO-66-NH ₂ Metal–Organic Framework (MOF) Nucleation on TiO ₂ , ZnO, and Al ₂ O ₃ Atomic Layer Deposition-Treated Polymer Fibers: Role of Metal Oxide on MOF Growth and Catalytic Hydrolysis of Chemical Warfare Agent Simulants
journal, December 2017

Cross-linking Zr-based metal–organic polyhedra via postsynthetic polymerization
journal, January 2017

The Chemistry and Applications of Metal-Organic Frameworks
journal, August 2013

In Situ Modification of Metal-Organic Frameworks in Mixed-Matrix Membranes
journal, June 2015

Metal–organic frameworks for membrane-based separations
journal, November 2016

Metal–organic frameworks for the removal of toxic industrial chemicals and chemical warfare agents
journal, January 2017

Enhanced aging properties of HKUST-1 in hydrophobic mixed-matrix membranes for ammonia adsorption
journal, January 2016

The Postsynthetic Renaissance in Porous Solids
journal, February 2017

Presence versus Proximity: The Role of Pendant Amines in the Catalytic Hydrolysis of a Nerve Agent Simulant
journal, January 2018

Photoinduced Postsynthetic Polymerization of a Metal-Organic Framework toward a Flexible Stand-Alone Membrane
journal, March 2015

High-throughput screening of solid-state catalysts for nerve agent degradation
journal, January 2018

Structure and crystallization behavior of Nylon 66/multi-walled carbon nanotube nanocomposites at low carbon nanotube contents
journal, June 2007