Accelerating Membrane-based CO2 Separation by Soluble Nanoporous Polymer Networks Produced by Mechanochemical Oxidative Coupling

Zhu, Xiang; Hua, Yinying; Tian, Chengcheng C.; Abney, Carter W.; Zhang, Peng; Jin, Tian; Liu, Gongping; Browning, Katie L.; Sacci, Robert L.; Veith, Gabriel M.; Zhou, Hong-Cai; Jin, Wanqin Q.; Dai, Sheng

doi:10.1002/anie.201710420

Title: Accelerating Membrane-based CO₂ Separation by Soluble Nanoporous Polymer Networks Produced by Mechanochemical Oxidative Coupling

Journal Article · Fri Dec 29 00:00:00 EST 2017 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201710420· OSTI ID:1462862

^[1]; Hua, Yinying ^[2]; Tian, Chengcheng C. ^[3];

^[4]; Zhang, Peng ^[5]; Jin, Tian ^[3]; Liu, Gongping ^[6]; Browning, Katie L. ^[7];

^[7];

^[7]; Zhou, Hong-Cai ^[5]; Jin, Wanqin Q. ^[6];

^[8]

Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry; Texas A & M Univ., College Station, TX (United States). Dept. of Chemistry
Nanjing Tech Univ., Nanjing (China). State Key Lab. of Materials-Oriented Chemical Engineering Jiangsu National Synergetic Innovation Center for Advanced Materials
Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
Texas A & M Univ., College Station, TX (United States). Dept. of Chemistry
Nanjing Tech Univ., Nanjing (China). State Key Lab. of Materials-Oriented Chemical Engineering Jiangsu National Synergetic Innovation Center for Advanced Materials
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Materials Science & Technology Division
Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry; Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division

Achieving homogeneous dispersion of nanoporous fillers within membrane architectures remains a great challenge for mixed-matrix membrane (MMMs) technology. Imparting solution processability of nanoporous materials would help advance the development of MMMs for membrane-based gas separations. A mechanochemically assisted oxidative coupling polymerization strategy was used to create a new family of soluble nanoporous polymer networks. The solid-state ball-milling method affords inherent molecular weight control over polymer growth and therefore provides unexpected solubility for the resulting nanoporous frameworks. MMM-based CO₂/CH₄ separation performance was significantly accelerated by these new soluble fillers. In conclusion, we anticipate this facile method will facilitate new possibilities for the rational design and synthesis of soluble nanoporous polymer networks and promote their applications in membrane-based gas separations.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1462862

Journal Information:: Angewandte Chemie (International Edition), Vol. 57, Issue 11; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 34 works

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References (56)

New Tricks for Old Molecules: Development and Application of Porous N-doped, Carbonaceous Membranes for CO ₂ Separation Zhu, Xiang; Tian, Chengcheng; Chai, Songhai Advanced Materials, Vol. 25, Issue 30 https://doi.org/10.1002/adma.201300793	journal	May 2013
Size-Controlled Synthesis of Conjugated Polymer Nanoparticles in Confined Nanoreactors Deng, Sheng; Zhi, Jian; Zhang, Xianmei Angewandte Chemie International Edition, Vol. 53, Issue 51 https://doi.org/10.1002/anie.201407387	journal	October 2014
Two-Dimensional Materials as Prospective Scaffolds for Mixed-Matrix Membrane-Based CO ₂ Separation Zhu, Xiang; Tian, Chengcheng; Do-Thanh, Chi-Linh ChemSusChem, Vol. 10, Issue 17 https://doi.org/10.1002/cssc.201700801	journal	August 2017
State-of-the-art membrane based CO2 separation using mixed matrix membranes (MMMs): An overview on current status and future directions Rezakazemi, Mashallah; Ebadi Amooghin, Abtin; Montazer-Rahmati, Mohammad Mehdi Progress in Polymer Science, Vol. 39, Issue 5 https://doi.org/10.1016/j.progpolymsci.2014.01.003	journal	May 2014
Hypercrosslinked Additives for Ageless Gas-Separation Membranes Lau, Cher Hon; Mulet, Xavier; Konstas, Kristina Angewandte Chemie, Vol. 128, Issue 6 https://doi.org/10.1002/ange.201508070	journal	January 2016
Porous Organic Polymers for Post-Combustion Carbon Capture Zou, Lanfang; Sun, Yujia; Che, Sai Advanced Materials, Vol. 29, Issue 37 https://doi.org/10.1002/adma.201700229	journal	July 2017
Oxidative coupling reactions of phenols with iron(III) chloride in the solid state Toda, Fumio; Tanaka, Koichi; Iwata, Shinji The Journal of Organic Chemistry, Vol. 54, Issue 13 https://doi.org/10.1021/jo00274a007	journal	June 1989
Two-Dimensional-Material Membranes: A New Family of High-Performance Separation Membranes Liu, Gongping; Jin, Wanqin; Xu, Nanping Angewandte Chemie International Edition, Vol. 55, Issue 43, p. 13384-13397 https://doi.org/10.1002/anie.201600438	journal	July 2016
Mechanochemical Friedel-Crafts Alkylation-A Sustainable Pathway Towards Porous Organic Polymers Troschke, Erik; Grätz, Sven; Lübken, Tilo Angewandte Chemie, Vol. 129, Issue 24 https://doi.org/10.1002/ange.201702303	journal	May 2017
Carbon Dioxide Capture: Prospects for New Materials D'Alessandro, Deanna M.; Smit, Berend; Long, Jeffrey R. Angewandte Chemie International Edition, Vol. 49, Issue 35, p. 6058-6082 https://doi.org/10.1002/anie.201000431	journal	July 2010
Solid-State Synthesis of Conjugated Nanoporous Polycarbazoles Zhu, Xiang; Tian, Chengcheng; Jin, Tian ACS Macro Letters, Vol. 6, Issue 10 https://doi.org/10.1021/acsmacrolett.7b00480	journal	September 2017
Gas-Separation Membranes Loaded with Porous Aromatic Frameworks that Improve with Age Lau, Cher Hon; Konstas, Kristina; Thornton, Aaron W. Angewandte Chemie International Edition, Vol. 54, Issue 9 https://doi.org/10.1002/anie.201410684	journal	January 2015
Enhanced selectivity in mixed matrix membranes for CO2 capture through efficient dispersion of amine-functionalized MOF nanoparticles Ghalei, Behnam; Sakurai, Kento; Kinoshita, Yosuke Nature Energy, Vol. 2, Issue 7 https://doi.org/10.1038/nenergy.2017.86	journal	June 2017
Polymeric Gas Separation Membranes Yampolskii, Yuri Macromolecules, Vol. 45, Issue 8 https://doi.org/10.1021/ma300213b	journal	March 2012
Advances in high permeability polymeric membrane materials for CO₂ separations Du, Naiying; Park, Ho Bum; Dal-Cin, Mauro M. Energy & Environmental Science, Vol. 5, Issue 6, p. 7306-7322 https://doi.org/10.1039/C1EE02668B	journal	January 2012
Mechanochemical Friedel-Crafts Alkylation-A Sustainable Pathway Towards Porous Organic Polymers Troschke, Erik; Grätz, Sven; Lübken, Tilo Angewandte Chemie International Edition, Vol. 56, Issue 24 https://doi.org/10.1002/anie.201702303	journal	May 2017
Membranen aus zweidimensionalen Materialien: eine neue Familie hochleistungsfähiger Trennmembranen Liu, Gongping; Jin, Wanqin; Xu, Nanping Angewandte Chemie, Vol. 128, Issue 43 https://doi.org/10.1002/ange.201600438	journal	July 2016
Polymers of Intrinsic Microporosity (PIMs): Bridging the Void between Microporous and Polymeric Materials McKeown, Neil B.; Budd, Peter M.; Msayib, Kadhum J. Chemistry - A European Journal, Vol. 11, Issue 9, p. 2610-2620 https://doi.org/10.1002/chem.200400860	journal	April 2005
Abscheidung von Kohlendioxid: Perspektiven für neue Materialien D'Alessandro, Deanna M.; Smit, Berend; Long, Jeffrey R. Angewandte Chemie, Vol. 122, Issue 35 https://doi.org/10.1002/ange.201000431	journal	July 2010
Metal–organic frameworks for membrane-based separations Denny, Michael S.; Moreton, Jessica C.; Benz, Lauren Nature Reviews Materials, Vol. 1, Issue 12 https://doi.org/10.1038/natrevmats.2016.78	journal	November 2016
Gas-Separation Membranes Loaded with Porous Aromatic Frameworks that Improve with Age Lau, Cher Hon; Konstas, Kristina; Thornton, Aaron W. Angewandte Chemie, Vol. 127, Issue 9 https://doi.org/10.1002/ange.201410684	journal	January 2015
Conjugated Microporous Poly(aryleneethynylene) Networks Jiang, Jia-Xing; Su, Fabing; Trewin, Abbie Angewandte Chemie, Vol. 119, Issue 45 https://doi.org/10.1002/ange.200701595	journal	November 2007
A Superacid-Catalyzed Synthesis of Porous Membranes Based on Triazine Frameworks for CO₂ Separation Zhu, Xiang; Tian, Chengcheng; Mahurin, Shannon M. Journal of the American Chemical Society, Vol. 134, Issue 25, p. 10478-10484 https://doi.org/10.1021/ja304879c	journal	June 2012
Ionothermalsynthese von porösen kovalenten Triazin- Polymernetzwerken Kuhn, Pierre; Antonietti, Markus; Thomas, Arne Angewandte Chemie, Vol. 120, Issue 18 https://doi.org/10.1002/ange.200705710	journal	April 2008
Function-led design of new porous materials Slater, A. G.; Cooper, A. I. Science, Vol. 348, Issue 6238 https://doi.org/10.1126/science.aaa8075	journal	May 2015
Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage McKeown, Neil B.; Budd, Peter M. Chemical Society Reviews, Vol. 35, Issue 8, p. 675-683 https://doi.org/10.1039/b600349d	journal	January 2006
Substitution Effect Guided Synthesis of Task-Specific Nanoporous Polycarbazoles with Enhanced Carbon Capture Jiang, Feng; Jin, Tian; Zhu, Xiang Macromolecules, Vol. 49, Issue 15 https://doi.org/10.1021/acs.macromol.6b01342	journal	July 2016
Mixed matrix membranes (MMMs) comprising organic polymers with dispersed inorganic fillers for gas separation Chung, Tai-Shung; Jiang, Lan Ying; Li, Yi Progress in Polymer Science, Vol. 32, Issue 4, p. 483-507 https://doi.org/10.1016/j.progpolymsci.2007.01.008	journal	April 2007
Nanoporous Organic Polymer/Cage Composite Membranes Bushell, Alexandra F.; Budd, Peter M.; Attfield, Martin P. Angewandte Chemie International Edition, Vol. 52, Issue 4 https://doi.org/10.1002/anie.201206339	journal	December 2012
Metal-organic framework nanosheets as building blocks for molecular sieving membranes Peng, Y.; Li, Y.; Ban, Y. Science, Vol. 346, Issue 6215 https://doi.org/10.1126/science.1254227	journal	December 2014
Advances in high permeability polymer-based membrane materials for CO ₂ separations Wang, Shaofei; Li, Xueqin; Wu, Hong Energy & Environmental Science, Vol. 9, Issue 6 https://doi.org/10.1039/C6EE00811A	journal	January 2016
Rational design and synthesis of a porous, task-specific polycarbazole for efficient CO ₂ capture Jin, Tian; Xiong, Yan; Zhu, Xiang Chemical Communications, Vol. 52, Issue 24 https://doi.org/10.1039/C6CC00573J	journal	January 2016
Soluble Porous Coordination Polymers by Mechanochemistry: From Metal-Containing Films/Membranes to Active Catalysts for Aerobic Oxidation Zhang, Pengfei; Li, Haiying; Veith, Gabriel M. Advanced Materials, Vol. 27, Issue 2 https://doi.org/10.1002/adma.201403299	journal	November 2014
Materials for next-generation molecularly selective synthetic membranes Koros, William J.; Zhang, Chen Nature Materials, Vol. 16, Issue 3 https://doi.org/10.1038/nmat4805	journal	January 2017
Mechanochemical Synthesis of Chemically Stable Isoreticular Covalent Organic Frameworks Biswal, Bishnu P.; Chandra, Suman; Kandambeth, Sharath Journal of the American Chemical Society, Vol. 135, Issue 14 https://doi.org/10.1021/ja4017842	journal	March 2013
Porous, Covalent Triazine-Based Frameworks Prepared by Ionothermal Synthesis Kuhn, Pierre; Antonietti, Markus; Thomas, Arne Angewandte Chemie International Edition, Vol. 47, Issue 18 https://doi.org/10.1002/anie.200705710	journal	April 2008
Simulated swelling during low-temperature N ₂ adsorption in polymers of intrinsic microporosity Hart, Kyle E.; Springmeier, Jeffrey M.; McKeown, Neil B. Phys. Chem. Chem. Phys., Vol. 15, Issue 46 https://doi.org/10.1039/C3CP53402B	journal	January 2013
Energy-efficient polymeric gas separation membranes for a sustainable future: A review Sanders, David F.; Smith, Zachary P.; Guo, Ruilan Polymer, Vol. 54, Issue 18 https://doi.org/10.1016/j.polymer.2013.05.075	journal	August 2013
Mechanochemistry: A Force of Synthesis Do, Jean-Louis; Friščić, Tomislav ACS Central Science, Vol. 3, Issue 1 https://doi.org/10.1021/acscentsci.6b00277	journal	December 2016
Soluble Conjugated Microporous Polymers Cheng, Ge; Hasell, Tom; Trewin, Abbie Angewandte Chemie, Vol. 124, Issue 51 https://doi.org/10.1002/ange.201205521	journal	November 2012
Conjugated Microporous Poly(aryleneethynylene) Networks Jiang, Jia-Xing; Su, Fabing; Trewin, Abbie Angewandte Chemie International Edition, Vol. 46, Issue 45 https://doi.org/10.1002/anie.200701595	journal	September 2007
Soluble Metal-Nanoparticle-Decorated Porous Coordination Polymers for the Homogenization of Heterogeneous Catalysis Huang, Yuan-Biao; Wang, Qiang; Liang, Jun Journal of the American Chemical Society, Vol. 138, Issue 32 https://doi.org/10.1021/jacs.6b06185	journal	August 2016
Mechanochemistry: opportunities for new and cleaner synthesis James, Stuart L.; Adams, Christopher J.; Bolm, Carsten Chem. Soc. Rev., Vol. 41, Issue 1 https://doi.org/10.1039/C1CS15171A	journal	January 2012
Nanoporous Organic Polymer/Cage Composite Membranes Bushell, Alexandra F.; Budd, Peter M.; Attfield, Martin P. Angewandte Chemie, Vol. 125, Issue 4 https://doi.org/10.1002/ange.201206339	journal	December 2012
In Situ Doping Strategy for the Preparation of Conjugated Triazine Frameworks Displaying Efficient CO ₂ Capture Performance Zhu, Xiang; Tian, Chengcheng; Veith, Gabriel M. Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b07644	journal	September 2016
Microporous Polycarbazole with High Specific Surface Area for Gas Storage and Separation Chen, Qi; Luo, Min; Hammershøj, Peter Journal of the American Chemical Society, Vol. 134, Issue 14 https://doi.org/10.1021/ja300438w	journal	March 2012
Cooperative insertion of CO2 in diamine-appended metal-organic frameworks McDonald, Thomas M.; Mason, Jarad A.; Kong, Xueqian Nature, Vol. 519, Issue 7543 https://doi.org/10.1038/nature14327	journal	March 2015
Hypercrosslinked Additives for Ageless Gas-Separation Membranes Lau, Cher Hon; Mulet, Xavier; Konstas, Kristina Angewandte Chemie International Edition, Vol. 55, Issue 6 https://doi.org/10.1002/anie.201508070	journal	January 2016
Metal–organic framework based mixed matrix membranes: a solution for highly efficient CO ₂ capture? Seoane, Beatriz; Coronas, Joaquin; Gascon, Ignacio Chemical Society Reviews, Vol. 44, Issue 8 https://doi.org/10.1039/C4CS00437J	journal	January 2015
The Chemistry of CO ₂ Capture in an Amine-Functionalized Metal–Organic Framework under Dry and Humid Conditions Flaig, Robinson W.; Osborn Popp, Thomas M.; Fracaroli, Alejandro M. Journal of the American Chemical Society, Vol. 139, Issue 35 https://doi.org/10.1021/jacs.7b06382	journal	August 2017
Covalent Organic Frameworks for CO ₂ Capture Zeng, Yongfei; Zou, Ruqiang; Zhao, Yanli Advanced Materials, Vol. 28, Issue 15 https://doi.org/10.1002/adma.201505004	journal	February 2016
Size-Controlled Synthesis of Conjugated Polymer Nanoparticles in Confined Nanoreactors Deng, Sheng; Zhi, Jian; Zhang, Xianmei Angewandte Chemie, Vol. 126, Issue 51 https://doi.org/10.1002/ange.201407387	journal	October 2014
Membranes with Fast and Selective Gas-Transport Channels of Laminar Graphene Oxide for Efficient CO ₂ Capture Shen, Jie; Liu, Gongping; Huang, Kang Angewandte Chemie, Vol. 127, Issue 2 https://doi.org/10.1002/ange.201409563	journal	November 2014
Soluble Conjugated Microporous Polymers Cheng, Ge; Hasell, Tom; Trewin, Abbie Angewandte Chemie International Edition, Vol. 51, Issue 51 https://doi.org/10.1002/anie.201205521	journal	November 2012
Conjugated Polymers of Intrinsic Microporosity (C-PIMs) Cheng, Ge; Bonillo, Baltasar; Sprick, Reiner S. Advanced Functional Materials, Vol. 24, Issue 33 https://doi.org/10.1002/adfm.201401001	journal	June 2014
Highly permeable polymers for gas separation membranes Budd, Peter M.; McKeown, Neil B. Polymer Chemistry, Vol. 1, Issue 1 https://doi.org/10.1039/b9py00319c	journal	January 2010

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36 MATERIALS SCIENCE
CO2/CH4 separation
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oxidative coupling polymerization
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Title: Accelerating Membrane-based CO2 Separation by Soluble Nanoporous Polymer Networks Produced by Mechanochemical Oxidative Coupling

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