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Title: Amine-functionalized porous organic polymers for carbon dioxide capture

Abstract

Recent developments in CO2 capture using porous organic polymers (POPs) have received accrescent attention due to their sorbent properties such as high CO2 uptake capacity and selectivity, tunable chemical structure and permanent porosity. POPs are constructed using two and/or three-dimensional organic monomers (building blocks) linked to each other through covalent bonding, creating high porosity. The pore structure in POPs is exceptionally stable, which leads to their cyclable CO2 adsorption performance. However, POPs generally suffer from low CO2 uptake and selectivity due to their interaction with CO2 in physisorption limits (20–40 kJ mol-1). Similar to that in other physisorbents, the CO2 uptake capacity of POPs further decreases under humid conditions. Pursuant to these limitations, amine functionalization in POPs has resulted in enhanced CO2 uptake performance with improved CO2 selectivity over non-polar gases such as N2. More importantly, several types of amine-functionalized POPs showed that the CO2 uptake could remain intact under humid conditions such as in post-combustion flue gas. This review article covers recent developments in amine-functionalized porous organic polymers. Three main categories of amine functionalization, such as direct amine synthesis, amine impregnation and amine grafting, were investigated in detail by considering the effect of amines on the sorbent properties andmore » CO2 capture performance of POPs. The recent findings in amine-functionalized POPs were investigated including porous polymeric networks (PPNs), covalent organic frameworks (COFs), amine linked POPs, hyper-crosslinked polymers (HCPs), conjugated microporous polymers (CMPs), benzimidazole linked polymers (BILPs), porous aromatic frameworks (PAFs) and polymers of intrinsic microporosity (PIMs).« less

Authors:
ORCiD logo [1];  [1];  [1];  [1];  [1]
  1. National Energy Technology Lab. (NETL), Pittsburgh, PA (United States)
Publication Date:
Research Org.:
National Energy Technology Laboratory (NETL), Pittsburgh, PA, Morgantown, WV, and Albany, OR (United States)
Sponsoring Org.:
USDOE Office of Fossil Energy (FE)
OSTI Identifier:
1888542
Resource Type:
Accepted Manuscript
Journal Name:
Materials Advances
Additional Journal Information:
Journal Volume: 3; Journal Issue: 17; Journal ID: ISSN 2633-5409
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Sekizkardes, Ali K., Wang, Ping, Hoffman, James, Budhathoki, Samir, and Hopkinson, David. Amine-functionalized porous organic polymers for carbon dioxide capture. United States: N. p., 2022. Web. doi:10.1039/d2ma00235c.
Sekizkardes, Ali K., Wang, Ping, Hoffman, James, Budhathoki, Samir, & Hopkinson, David. Amine-functionalized porous organic polymers for carbon dioxide capture. United States. https://doi.org/10.1039/d2ma00235c
Sekizkardes, Ali K., Wang, Ping, Hoffman, James, Budhathoki, Samir, and Hopkinson, David. Wed . "Amine-functionalized porous organic polymers for carbon dioxide capture". United States. https://doi.org/10.1039/d2ma00235c. https://www.osti.gov/servlets/purl/1888542.
@article{osti_1888542,
title = {Amine-functionalized porous organic polymers for carbon dioxide capture},
author = {Sekizkardes, Ali K. and Wang, Ping and Hoffman, James and Budhathoki, Samir and Hopkinson, David},
abstractNote = {Recent developments in CO2 capture using porous organic polymers (POPs) have received accrescent attention due to their sorbent properties such as high CO2 uptake capacity and selectivity, tunable chemical structure and permanent porosity. POPs are constructed using two and/or three-dimensional organic monomers (building blocks) linked to each other through covalent bonding, creating high porosity. The pore structure in POPs is exceptionally stable, which leads to their cyclable CO2 adsorption performance. However, POPs generally suffer from low CO2 uptake and selectivity due to their interaction with CO2 in physisorption limits (20–40 kJ mol-1). Similar to that in other physisorbents, the CO2 uptake capacity of POPs further decreases under humid conditions. Pursuant to these limitations, amine functionalization in POPs has resulted in enhanced CO2 uptake performance with improved CO2 selectivity over non-polar gases such as N2. More importantly, several types of amine-functionalized POPs showed that the CO2 uptake could remain intact under humid conditions such as in post-combustion flue gas. This review article covers recent developments in amine-functionalized porous organic polymers. Three main categories of amine functionalization, such as direct amine synthesis, amine impregnation and amine grafting, were investigated in detail by considering the effect of amines on the sorbent properties and CO2 capture performance of POPs. The recent findings in amine-functionalized POPs were investigated including porous polymeric networks (PPNs), covalent organic frameworks (COFs), amine linked POPs, hyper-crosslinked polymers (HCPs), conjugated microporous polymers (CMPs), benzimidazole linked polymers (BILPs), porous aromatic frameworks (PAFs) and polymers of intrinsic microporosity (PIMs).},
doi = {10.1039/d2ma00235c},
journal = {Materials Advances},
number = 17,
volume = 3,
place = {United States},
year = {Wed Jun 15 00:00:00 EDT 2022},
month = {Wed Jun 15 00:00:00 EDT 2022}
}

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  • New Journal of Chemistry, Vol. 41, Issue 14
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Porous organic polymers with anchored aldehydes: a new platform for post-synthetic amine functionalization en route for enhanced CO2 adsorption properties
journal, January 2014

  • Guillerm, Vincent; Weseliński, Łukasz J.; Alkordi, Mohamed
  • Chemical Communications, Vol. 50, Issue 16
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Evaluation of porous adsorbents for CO2 capture under humid conditions: The importance of recyclability
journal, November 2020


Imine-Linked Porous Polymer Frameworks with High Small Gas (H 2 , CO 2 , CH 4 , C 2 H 2 ) Uptake and CO 2 /N 2 Selectivity
journal, April 2013

  • Zhu, Youlong; Long, Hai; Zhang, Wei
  • Chemistry of Materials, Vol. 25, Issue 9
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Triptycene based and nitrogen rich hyper cross linked polymers (TNHCPs) as efficient CO2 and iodine adsorbent
journal, February 2021


Amine or Azo functionalized hypercrosslinked polymers for highly efficient CO2 capture and selective CO2 capture
journal, June 2021


Direct Capture of CO2 from Ambient Air
journal, August 2016

  • Sanz-Pérez, Eloy S.; Murdock, Christopher R.; Didas, Stephanie A.
  • Chemical Reviews, Vol. 116, Issue 19, p. 11840-11876
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Advances in CO2 capture technology: A patent review
journal, February 2013


CO2 Capture Using PIM-1 Hollow Fiber Sorbents with Enhanced Performance by PEI Infusion
journal, August 2021

  • Quan, Wenying; Zhang, Fengyi; Hamlett, Breanne L.
  • Industrial & Engineering Chemistry Research, Vol. 60, Issue 34
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Alkylamine-Tethered Stable Metal-Organic Framework for CO 2 Capture from Flue Gas
journal, January 2014


PIM-1 as a Solution-Processable “Molecular Basket” for CO 2 Capture from Dilute Sources
journal, November 2015


Overcoming mass transfer limitations in cross-linked polyethyleneimine-based adsorbents to enable selective CO2 capture at ambient temperature
journal, January 2022

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  • Materials Advances, Vol. 3, Issue 7
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Functional porous organic polymers for heterogeneous catalysis
journal, January 2012

  • Zhang, Yugen; Riduan, Siti Nurhanna
  • Chem. Soc. Rev., Vol. 41, Issue 6
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Chemical tuning of CO2 sorption in robust nanoporous organic polymers
journal, January 2011

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  • Chemical Science, Vol. 2, Issue 6
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Progress on CO2 capture by porous organic polymers
journal, April 2019


Introduction: Carbon Capture and Separation
journal, May 2017


Synthesis of 2D Imine-Linked Covalent Organic Frameworks through Formal Transimination Reactions
journal, September 2017

  • Vitaku, Edon; Dichtel, William R.
  • Journal of the American Chemical Society, Vol. 139, Issue 37
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Highly optimized CO 2 capture by inexpensive nanoporous covalent organic polymers and their amine composites
journal, January 2015

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  • Faraday Discussions, Vol. 183
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Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage
journal, January 2006

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Post-synthetic modification of fluorenone based hypercrosslinked porous copolymers for carbon dioxide capture
journal, July 2021


Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route
journal, November 2012

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  • Journal of the American Chemical Society, Vol. 134, Issue 48
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The atom, the molecule, and the covalent organic framework
journal, March 2017


An Azine-Linked Covalent Organic Framework: Synthesis, Characterization and Efficient Gas Storage
journal, July 2015

  • Li, Zhongping; Zhi, Yongfeng; Feng, Xiao
  • Chemistry - A European Journal, Vol. 21, Issue 34
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Remarkable gas adsorption by carbonized nitrogen-rich hypercrosslinked porous organic polymers
journal, January 2014

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  • J. Mater. Chem. A, Vol. 2, Issue 36
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Porous aromatic frameworks: Synthesis, structure and functions
journal, January 2013


Microporous Organic Polymers Based on Hyper-Crosslinked Coal Tar: Preparation and Application for Gas Adsorption
journal, January 2017


Lignin-based Microporous Materials as Selective Adsorbents for Carbon Dioxide Separation
journal, October 2014


Synthesis and Characterization of Porous Benzimidazole-Linked Polymers and Their Performance in Small Gas Storage and Selective Uptake
journal, April 2012

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  • Chemistry of Materials, Vol. 24, Issue 8
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Novel microporous hypercross-linked conjugated quinonoid chromophores with broad light absorption and CO2sorption characteristics
journal, January 2014

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Novel Porous Organic Polymer for the Concurrent and Selective Removal of Hydrogen Sulfide and Carbon Dioxide from Natural Gas Streams
journal, September 2020

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  • ACS Applied Materials & Interfaces, Vol. 12, Issue 42
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Imine-Linked Microporous Polymer Organic Frameworks
journal, September 2010

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  • Chemistry of Materials, Vol. 22, Issue 17
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A 2D Mesoporous Imine-Linked Covalent Organic Framework for High Pressure Gas Storage Applications
journal, February 2013

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  • Chemistry - A European Journal, Vol. 19, Issue 10
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Solving the COF trilemma: towards crystalline, stable and functional covalent organic frameworks
journal, January 2020

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  • Chemical Society Reviews, Vol. 49, Issue 23
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Nanoporous organic polymer networks
journal, April 2012


Unprecedented high-temperature CO2 selectivity in N2-phobic nanoporous covalent organic polymers
journal, January 2013

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Pyrene-directed growth of nanoporous benzimidazole-linked nanofibers and their application to selective CO2 capture and separation
journal, January 2012

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  • Journal of Materials Chemistry, Vol. 22, Issue 48
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Tailoring the pore size of hypercrosslinked polymers
journal, January 2011


Flue gas treatment via CO2 adsorption
journal, July 2011

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  • Chemical Engineering Journal, Vol. 171, Issue 3
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Porous Aromatic Frameworks as a Platform for Multifunctional Applications
journal, February 2019


Click Chemistry Finds Its Way into Covalent Porous Organic Materials
journal, November 2011

  • Muller, Thierry; Bräse, Stefan
  • Angewandte Chemie International Edition, Vol. 50, Issue 50
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Highly porous photoluminescent diazaborole-linked polymers: synthesis, characterization, and application to selective gas adsorption
journal, January 2017

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  • Polymer Chemistry, Vol. 8, Issue 16
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Emerging trends in porous materials for CO 2 capture and conversion
journal, January 2020

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Covalent Triazine Frameworks Prepared from 1,3,5-Tricyanobenzene
journal, April 2013

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  • Chemistry of Materials, Vol. 25, Issue 9
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Polymers of Intrinsic Microporosity Chemical Sorbents Utilizing Primary Amine Appendance Through Acid–Base and Hydrogen-Bonding Interactions
journal, August 2019

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  • ACS Applied Materials & Interfaces, Vol. 11, Issue 34
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