skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Charged Porous Polymers using a Solid C-O Cross-Coupling Reaction

Abstract

Here in this paper, we report a green, fast, efficient mechanochemical strategy for charged porous polymers (CPPs). A cationic CPP with basic anions and an anionic CPP with Li+ cations were fabricated by solid grinding under solvent-free conditions. Compared with solution-based synthesis, mechanochemical grinding can shorten the reaction time from dozens of hours to several minutes (60–90 min) to form polymers possessing a high molecular mass and low polydispersity. During the construction of CPPs, a Pd-catalyzed solid polycondensation based on unactivated organic linkers was introduced. In particular, CPPs with basic phenolic or proline anions showed good activity and stability in SO2 capture, and Li+-functionalized CPPs can be post-modified to CPPs with other metal ions by ion exchange, highlighting the tailorable feature of ionic-modified CPPs.

Authors:
; ; ;
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Fluid Interface Reactions, Structures and Transport Center (FIRST)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1386260
DOE Contract Number:  
ERKCC61
Resource Type:
Journal Article
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 21; Journal Issue: 37; Related Information: FIRST partners with Oak Ridge National Laboratory (lead); Argonne National Laboratory; Drexel University; Georgia State University; Northwestern University; Pennsylvania State University; Suffolk University; Vanderbilt University; University of Virginia; Journal ID: ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
catalysis (heterogeneous), solar (fuels), energy storage (including batteries and capacitors), hydrogen and fuel cells, electrodes - solar, mechanical behavior, charge transport, materials and chemistry by design, synthesis (novel materials)

Citation Formats

Zhang, Pengfei, Jiang, Xueguang, Wan, Shun, and Dai, Sheng. Charged Porous Polymers using a Solid C-O Cross-Coupling Reaction. United States: N. p., 2015. Web. doi:10.1002/chem.201501814.
Zhang, Pengfei, Jiang, Xueguang, Wan, Shun, & Dai, Sheng. Charged Porous Polymers using a Solid C-O Cross-Coupling Reaction. United States. doi:10.1002/chem.201501814.
Zhang, Pengfei, Jiang, Xueguang, Wan, Shun, and Dai, Sheng. Wed . "Charged Porous Polymers using a Solid C-O Cross-Coupling Reaction". United States. doi:10.1002/chem.201501814.
@article{osti_1386260,
title = {Charged Porous Polymers using a Solid C-O Cross-Coupling Reaction},
author = {Zhang, Pengfei and Jiang, Xueguang and Wan, Shun and Dai, Sheng},
abstractNote = {Here in this paper, we report a green, fast, efficient mechanochemical strategy for charged porous polymers (CPPs). A cationic CPP with basic anions and an anionic CPP with Li+ cations were fabricated by solid grinding under solvent-free conditions. Compared with solution-based synthesis, mechanochemical grinding can shorten the reaction time from dozens of hours to several minutes (60–90 min) to form polymers possessing a high molecular mass and low polydispersity. During the construction of CPPs, a Pd-catalyzed solid polycondensation based on unactivated organic linkers was introduced. In particular, CPPs with basic phenolic or proline anions showed good activity and stability in SO2 capture, and Li+-functionalized CPPs can be post-modified to CPPs with other metal ions by ion exchange, highlighting the tailorable feature of ionic-modified CPPs.},
doi = {10.1002/chem.201501814},
journal = {Chemistry - A European Journal},
issn = {0947-6539},
number = 37,
volume = 21,
place = {United States},
year = {2015},
month = {7}
}

Works referenced in this record:

Design and Preparation of Porous Polymers
journal, April 2012

  • Wu, Dingcai; Xu, Fei; Sun, Bin
  • Chemical Reviews, Vol. 112, Issue 7
  • DOI: 10.1021/cr200440z

Solvent‐Free Synthesis of Silicoaluminophosphate Zeolites
journal, July 2013


Catalyst-free Preparation of Melamine-Based Microporous Polymer Networks through Schiff Base Chemistry
journal, June 2009

  • Schwab, Matthias Georg; Fassbender, Birgit; Spiess, Hans Wolfgang
  • Journal of the American Chemical Society, Vol. 131, Issue 21
  • DOI: 10.1021/ja902116f

Anionische, mikroporöse Polymernetzwerke durch Polymerisation eines schwach koordinierenden Anions
journal, September 2013

  • Fischer, Sabrina; Schmidt, Johannes; Strauch, Peter
  • Angewandte Chemie, Vol. 125, Issue 46
  • DOI: 10.1002/ange.201303045

A polymer analogous reaction for the formation of imidazolium and NHC based porous polymer networks
journal, January 2013

  • Thiel, Kerstin; Zehbe, Rolf; Roeser, Jerômé
  • Polymer Chemistry, Vol. 4, Issue 6
  • DOI: 10.1039/c2py20947k

Solvent-free synthesis of metal complexes
journal, January 2007

  • Garay, Ana Lazuen; Pichon, Anne; James, Stuart L.
  • Chemical Society Reviews, Vol. 36, Issue 6
  • DOI: 10.1039/b600363j

Highly Stable Porous Polymer Networks with Exceptionally High Gas-Uptake Capacities
journal, July 2011


Cation Cross-Linked Ionic Liquids as Anion-Exchange Materials
journal, October 2009

  • Lee, Je Seung; Luo, Huimin; Baker, Gary A.
  • Chemistry of Materials, Vol. 21, Issue 20
  • DOI: 10.1021/cm902522b

Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose
journal, March 2013

  • Zhang, Pengfei; Gong, Yutong; Li, Haoran
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms2586

Mesoporous zwitterionic poly(ionic liquid)s: intrinsic complexation and efficient catalytic fixation of CO2
journal, January 2013

  • Soll, Sebastian; Zhang, Pengfei; Zhao, Qiang
  • Polymer Chemistry, Vol. 4, Issue 19
  • DOI: 10.1039/c3py00823a

Chemically Stable Multilayered Covalent Organic Nanosheets from Covalent Organic Frameworks via Mechanical Delamination
journal, November 2013

  • Chandra, Suman; Kandambeth, Sharath; Biswal, Bishnu P.
  • Journal of the American Chemical Society, Vol. 135, Issue 47
  • DOI: 10.1021/ja408121p

Equimolar CO2 Absorption by Anion-Functionalized Ionic Liquids
journal, February 2010

  • Gurkan, Burcu E.; de la Fuente, Juan C.; Mindrup, Elaine M.
  • Journal of the American Chemical Society, Vol. 132, Issue 7, p. 2116-2117
  • DOI: 10.1021/ja909305t

Advancing polymers of intrinsic microporosity by mechanochemistry
journal, January 2015

  • Zhang, Pengfei; Jiang, Xueguang; Wan, Shun
  • Journal of Materials Chemistry A, Vol. 3, Issue 13
  • DOI: 10.1039/C4TA07196D

Ion- and Liquid-Assisted Grinding: Improved Mechanochemical Synthesis of Metal-Organic Frameworks Reveals Salt Inclusion and Anion Templating
journal, December 2009

  • Friščić, Tomislav; Reid, David G.; Halasz, Ivan
  • Angewandte Chemie, Vol. 122, Issue 4
  • DOI: 10.1002/ange.200906583

Supramolecular Catalysis in the Organic Solid State through Dry Grinding
journal, May 2010

  • Sokolov, Anatoliy N.; Bučar, Dejan-Krešimir; Baltrusaitis, Jonas
  • Angewandte Chemie International Edition, Vol. 49, Issue 25
  • DOI: 10.1002/anie.201000874

Conjugated porous polymers for energy applications
journal, January 2012

  • Vilela, Filipe; Zhang, Kai; Antonietti, Markus
  • Energy & Environmental Science, Vol. 5, Issue 7
  • DOI: 10.1039/c2ee22002d

Ion- and Liquid-Assisted Grinding: Improved Mechanochemical Synthesis of Metal-Organic Frameworks Reveals Salt Inclusion and Anion Templating
journal, December 2009

  • Friščić, Tomislav; Reid, David G.; Halasz, Ivan
  • Angewandte Chemie International Edition, Vol. 49, Issue 4
  • DOI: 10.1002/anie.200906583

Mechanosynthesis of imine, β-ketoenamine, and hydrogen-bonded imine-linked covalent organic frameworks using liquid-assisted grinding
journal, January 2014

  • Das, Gobinda; Balaji Shinde, Digambar; Kandambeth, Sharath
  • Chem. Commun., Vol. 50, Issue 84
  • DOI: 10.1039/C4CC03389B

Porous covalent–organic materials: synthesis, clean energy application and design
journal, January 2013


New insights into carbon dioxide interactions with benzimidazole-linked polymers
journal, January 2014

  • Altarawneh, Suha; Behera, S.; Jena, Puru
  • Chem. Commun., Vol. 50, Issue 27
  • DOI: 10.1039/C3CC45901B

Solution-Processed, Organophilic Membrane Derived from a Polymer of Intrinsic Microporosity
journal, March 2004

  • Budd, P. M.; Elabas, E. S.; Ghanem, B. S.
  • Advanced Materials, Vol. 16, Issue 5, p. 456-459
  • DOI: 10.1002/adma.200306053

Porous, Crystalline, Covalent Organic Frameworks
journal, November 2005

  • Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W.
  • Science, Vol. 310, Issue 5751, p. 1166-1170
  • DOI: 10.1126/science.1120411

Cationic microporous polymer networks by polymerisation of weakly coordinating cations with CO 2 -storage ability
journal, January 2014

  • Fischer, Sabrina; Schimanowitz, Aneta; Dawson, Robert
  • J. Mater. Chem. A, Vol. 2, Issue 30
  • DOI: 10.1039/C4TA02022G

Supramolecular Catalysis in the Organic Solid State through Dry Grinding
journal, May 2010

  • Sokolov, Anatoliy N.; Bučar, Dejan-Krešimir; Baltrusaitis, Jonas
  • Angewandte Chemie, Vol. 122, Issue 25
  • DOI: 10.1002/ange.201000874

Linear High Molecular Weight Ladder Polymer via Fast Polycondensation of 5,5′,6,6′-Tetrahydroxy-3,3,3′,3′-tetramethylspirobisindane with 1,4-Dicyanotetrafluorobenzene
journal, May 2008

  • Du, Naiying; Song, Jingshe; Robertson, Gilles P.
  • Macromolecular Rapid Communications, Vol. 29, Issue 10
  • DOI: 10.1002/marc.200800038

N-Heterocyclic carbene containing element organic frameworks as heterogeneous organocatalysts
journal, January 2011

  • Rose, Marcus; Notzon, Andreas; Heitbaum, Maja
  • Chemical Communications, Vol. 47, Issue 16
  • DOI: 10.1039/c1cc10268k

Poly(ionic liquid) Complex with Spontaneous Micro-/Mesoporosity: Template-Free Synthesis and Application as Catalyst Support
journal, July 2012

  • Zhao, Qiang; Zhang, Pengfei; Antonietti, Markus
  • Journal of the American Chemical Society, Vol. 134, Issue 29
  • DOI: 10.1021/ja303552p

Highly Efficient and Reversible SO 2 Capture by Tunable Azole-Based Ionic Liquids through Multiple-Site Chemical Absorption
journal, August 2011

  • Wang, Congmin; Cui, Guokai; Luo, Xiaoyan
  • Journal of the American Chemical Society, Vol. 133, Issue 31
  • DOI: 10.1021/ja204808h

Green Routes for Synthesis of Zeolites
journal, November 2013

  • Meng, Xiangju; Xiao, Feng-Shou
  • Chemical Reviews, Vol. 114, Issue 2
  • DOI: 10.1021/cr4001513

Ionothermalsynthese von porösen kovalenten Triazin- Polymernetzwerken
journal, April 2008

  • Kuhn, Pierre; Antonietti, Markus; Thomas, Arne
  • Angewandte Chemie, Vol. 120, Issue 18
  • DOI: 10.1002/ange.200705710

Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage
journal, January 2006

  • McKeown, Neil B.; Budd, Peter M.
  • Chemical Society Reviews, Vol. 35, Issue 8, p. 675-683
  • DOI: 10.1039/b600349d

Tubular microporous organic networks bearing imidazolium salts and their catalytic CO 2 conversion to cyclic carbonates
journal, January 2011

  • Cho, Hyun Chul; Lee, Han Sol; Chun, Jiseul
  • Chem. Commun., Vol. 47, Issue 3
  • DOI: 10.1039/C0CC03914D

Targeted Synthesis of a Porous Aromatic Framework with High Stability and Exceptionally High Surface Area
journal, November 2009

  • Ben, Teng; Ren, Hao; Ma, Shengqian
  • Angewandte Chemie International Edition, Vol. 48, Issue 50, p. 9457-9460
  • DOI: 10.1002/anie.200904637

Polymer nanosieve membranes for CO2-capture applications
journal, April 2011

  • Du, Naiying; Park, Ho Bum; Robertson, Gilles P.
  • Nature Materials, Vol. 10, Issue 5, p. 372-375
  • DOI: 10.1038/nmat2989

Hydrogen adsorption in lithium decorated conjugated microporous polymers: a DFT investigation
journal, January 2014


Lithium-Doped Conjugated Microporous Polymers for Reversible Hydrogen Storage
journal, March 2010

  • Li, An; Lu, Rui-Feng; Wang, Yi
  • Angewandte Chemie International Edition, Vol. 49, Issue 19
  • DOI: 10.1002/anie.200906936

Mechanochemical Synthesis of Chemically Stable Isoreticular Covalent Organic Frameworks
journal, March 2013

  • Biswal, Bishnu P.; Chandra, Suman; Kandambeth, Sharath
  • Journal of the American Chemical Society, Vol. 135, Issue 14
  • DOI: 10.1021/ja4017842

Porous, Covalent Triazine-Based Frameworks Prepared by Ionothermal Synthesis
journal, April 2008

  • Kuhn, Pierre; Antonietti, Markus; Thomas, Arne
  • Angewandte Chemie International Edition, Vol. 47, Issue 18
  • DOI: 10.1002/anie.200705710

Solvent-free synthesis of a microporous metal–organic framework
journal, January 2006

  • Pichon, Anne; Lazuen-Garay, Ana; James, Stuart L.
  • CrystEngComm, Vol. 8, Issue 3
  • DOI: 10.1039/b513750k

Ball milling in organic synthesis: solutions and challenges
journal, January 2011

  • Stolle, Achim; Szuppa, Tony; Leonhardt, Silke E. S.
  • Chemical Society Reviews, Vol. 40, Issue 5
  • DOI: 10.1039/c0cs00195c

Recent Development of Hypercrosslinked Microporous Organic Polymers
journal, January 2013

  • Xu, Shujun; Luo, Yali; Tan, Bien
  • Macromolecular Rapid Communications, Vol. 34, Issue 6
  • DOI: 10.1002/marc.201200788

New opportunities for materials synthesis using mechanochemistry
journal, January 2010

  • Friščić, Tomislav
  • Journal of Materials Chemistry, Vol. 20, Issue 36
  • DOI: 10.1039/c0jm00872a

Cyclic Ladder Polymers Based on 5,5‘,6,6‘-Tetrahydroxy-3,3,3‘,3‘-tetramethylspirobisindane and 2,3,5,6-Tetrafluoropyridines
journal, July 2006

  • Kricheldorf, Hans R.; Fritsch, Detlev; Vakhtangishvili, Lali
  • Macromolecules, Vol. 39, Issue 15
  • DOI: 10.1021/ma051398s

Easy Synthesis of Hollow Polymer, Carbon, and Graphitized Microspheres
journal, January 2010


Three-Dimensional Conformal Coatings through the Entrapment of Polymer Membrane Precursors
journal, February 2014

  • Nguyen, Du T.; Kleiman, Maya; Ryu, Keun Ah
  • ACS Applied Materials & Interfaces, Vol. 6, Issue 4
  • DOI: 10.1021/am4053943

Mechanochemistry: opportunities for new and cleaner synthesis
journal, January 2012

  • James, Stuart L.; Adams, Christopher J.; Bolm, Carsten
  • Chem. Soc. Rev., Vol. 41, Issue 1
  • DOI: 10.1039/C1CS15171A

Covalent organic frameworks
journal, January 2012

  • Feng, Xiao; Ding, Xuesong; Jiang, Donglin
  • Chemical Society Reviews, Vol. 41, Issue 18
  • DOI: 10.1039/c2cs35157a

An Anionic Microporous Polymer Network Prepared by the Polymerization of Weakly Coordinating Anions
journal, October 2013

  • Fischer, Sabrina; Schmidt, Johannes; Strauch, Peter
  • Angewandte Chemie International Edition, Vol. 52, Issue 46
  • DOI: 10.1002/anie.201303045

Enhanced Carbon Dioxide Adsorption by a Mesoporous Poly(ionic liquid)
journal, July 2012

  • Wilke, Antje; Yuan, Jiayin; Antonietti, Markus
  • ACS Macro Letters, Vol. 1, Issue 8
  • DOI: 10.1021/mz3003352

Solvent-Free Synthesis of Silicoaluminophosphate Zeolites
journal, July 2013

  • Jin, Yinying; Sun, Qi; Qi, Guodong
  • Angewandte Chemie International Edition, Vol. 52, Issue 35
  • DOI: 10.1002/anie.201302672

Thiophene-based covalent organic frameworks
journal, March 2013

  • Bertrand, G. H. V.; Michaelis, V. K.; Ong, T. -C.
  • Proceedings of the National Academy of Sciences, Vol. 110, Issue 13
  • DOI: 10.1073/pnas.1221824110

Improving Hydrothermal Carbonization by Using Poly(ionic liquid)s
journal, April 2013

  • Zhang, Pengfei; Yuan, Jiayin; Fellinger, Tim-Patrick
  • Angewandte Chemie International Edition, Vol. 52, Issue 23
  • DOI: 10.1002/anie.201301069

Easy Synthesis of Hollow Polymer, Carbon, and Graphitized Microspheres
journal, January 2010

  • Lu, An-Hui; Li, Wen-Cui; Hao, Guang-Ping
  • Angewandte Chemie International Edition, Vol. 49, Issue 9
  • DOI: 10.1002/anie.200906445

Microporous Polycarbazole with High Specific Surface Area for Gas Storage and Separation
journal, March 2012

  • Chen, Qi; Luo, Min; Hammershøj, Peter
  • Journal of the American Chemical Society, Vol. 134, Issue 14
  • DOI: 10.1021/ja300438w

Sulfonate-Grafted Porous Polymer Networks for Preferential CO2 Adsorption at Low Pressure
journal, November 2011

  • Lu, Weigang; Yuan, Daqiang; Sculley, Julian
  • Journal of the American Chemical Society, Vol. 133, Issue 45, p. 18126-18129
  • DOI: 10.1021/ja2087773

Mechanochemistry:  The Mechanical Activation of Covalent Bonds
journal, August 2005

  • Beyer, Martin K.; Clausen-Schaumann, Hauke
  • Chemical Reviews, Vol. 105, Issue 8
  • DOI: 10.1021/cr030697h

Targeted Synthesis of a Porous Aromatic Framework with High Stability and Exceptionally High Surface Area
journal, November 2009


Lithium-Doped Conjugated Microporous Polymers for Reversible Hydrogen Storage
journal, March 2010


Porous materials with pre-designed single-molecule traps for CO2 selective adsorption
journal, February 2013

  • Li, Jian-Rong; Yu, Jiamei; Lu, Weigang
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms2552

Conjugated Microporous Polymers
journal, March 2009


Synthesis of polyfluorinated aryl ethers via ligand-free palladium-catalyzed CF activation of pentafluorobenzene
journal, June 2013


Improving Hydrothermal Carbonization by Using Poly(ionic liquid)s
journal, April 2013

  • Zhang, Pengfei; Yuan, Jiayin; Fellinger, Tim-Patrick
  • Angewandte Chemie, Vol. 125, Issue 23
  • DOI: 10.1002/ange.201301069

Novel Functional Organic Network Containing Quaternary Phosphonium and Tertiary Phosphorus
journal, March 2012

  • Zhang, Qiang; Zhang, Suobo; Li, Shenghai
  • Macromolecules, Vol. 45, Issue 7
  • DOI: 10.1021/ma300278d

Transesterification Catalyzed by Ionic Liquids on Superhydrophobic Mesoporous Polymers: Heterogeneous Catalysts That Are Faster than Homogeneous Catalysts
journal, September 2012

  • Liu, Fujian; Wang, Liang; Sun, Qi
  • Journal of the American Chemical Society, Vol. 134, Issue 41
  • DOI: 10.1021/ja307455w