Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks
Abstract
Here, a series of structurally diverse alcoholamine- and alkoxyalkylamine-functionalized variants of the metal–organic framework Mg2(dobpdc) are shown to adsorb CO2 selectively via cooperative chain-forming mechanisms. Solid-state NMR spectra and optimized structures obtained from van der Waals-corrected density functional theory calculations indicate that the adsorption profiles can be attributed to the formation of carbamic acid or ammonium carbamate chains that are stabilized by hydrogen bonding interactions within the framework pores. These findings significantly expand the scope of chemical functionalities that can be utilized to design cooperative CO2 adsorbents, providing further means of optimizing these powerful materials for energy-efficient CO2 separations.
- Authors:
-
[1];
[2];
[3];
[4];
[5];
[6];
[5];
[8]
- Univ. of California, Berkeley, CA (United States). Dept. of Chemical and Biomolecular Engineering
- Cornell Univ., Ithaca, NY (United States). Dept. of Chemistry and Chemical Biology
- Univ. of California, Berkeley, CA (United States). Dept. of Physics and Kavli Energy Nanosciences Inst.; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry
- Univ. of California, Berkeley, CA (United States). Dept. of Chemical and Biomolecular Engineering and Dept. of Chemistry and Berkeley Energy and Climate Inst.
- Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
- Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Sciences Division
- Department of ChemistryThe University of California, Berkeley Berkeley CA 94720 USA
- Univ. of California, Berkeley, CA (United States). Dept. of Chemical and Biomolecular Engineering and Dept. of Chemistry
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE National Energy Technology Laboratory (NETL); National Institutes of Health (NIH)
- OSTI Identifier:
- 1634073
- Alternate Identifier(s):
- OSTI ID: 1597159
- Grant/Contract Number:
- AC02-05CH11231; SC0019992; FWP-00006194; F32GM120799
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie
- Additional Journal Information:
- Journal Volume: 132; Journal Issue: 44; Journal ID: ISSN 0044-8249
- Publisher:
- German Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; DFT-Berechnungen; Kohlendioxid; Kohlenstoffbindung; Metall-organische Gerüste; NMR-Spektroskopie
Citation Formats
Mao, Victor Y., Milner, Phillip J., Lee, Jung‐Hoon, Forse, Alexander C., Kim, Eugene J., Siegelman, Rebecca L., McGuirk, C. Michael, Porter‐Zasada, Leo B., Neaton, Jeffrey B., Reimer, Jeffrey A., and Long, Jeffrey R. Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks. United States: N. p., 2019.
Web. doi:10.1002/ange.201915561.
Mao, Victor Y., Milner, Phillip J., Lee, Jung‐Hoon, Forse, Alexander C., Kim, Eugene J., Siegelman, Rebecca L., McGuirk, C. Michael, Porter‐Zasada, Leo B., Neaton, Jeffrey B., Reimer, Jeffrey A., & Long, Jeffrey R. Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks. United States. https://doi.org/10.1002/ange.201915561
Mao, Victor Y., Milner, Phillip J., Lee, Jung‐Hoon, Forse, Alexander C., Kim, Eugene J., Siegelman, Rebecca L., McGuirk, C. Michael, Porter‐Zasada, Leo B., Neaton, Jeffrey B., Reimer, Jeffrey A., and Long, Jeffrey R. Thu .
"Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks". United States. https://doi.org/10.1002/ange.201915561. https://www.osti.gov/servlets/purl/1634073.
@article{osti_1634073,
title = {Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks},
author = {Mao, Victor Y. and Milner, Phillip J. and Lee, Jung‐Hoon and Forse, Alexander C. and Kim, Eugene J. and Siegelman, Rebecca L. and McGuirk, C. Michael and Porter‐Zasada, Leo B. and Neaton, Jeffrey B. and Reimer, Jeffrey A. and Long, Jeffrey R.},
abstractNote = {Here, a series of structurally diverse alcoholamine- and alkoxyalkylamine-functionalized variants of the metal–organic framework Mg2(dobpdc) are shown to adsorb CO2 selectively via cooperative chain-forming mechanisms. Solid-state NMR spectra and optimized structures obtained from van der Waals-corrected density functional theory calculations indicate that the adsorption profiles can be attributed to the formation of carbamic acid or ammonium carbamate chains that are stabilized by hydrogen bonding interactions within the framework pores. These findings significantly expand the scope of chemical functionalities that can be utilized to design cooperative CO2 adsorbents, providing further means of optimizing these powerful materials for energy-efficient CO2 separations.},
doi = {10.1002/ange.201915561},
journal = {Angewandte Chemie},
number = 44,
volume = 132,
place = {United States},
year = {2019},
month = {12}
}
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Works referenced in this record:
The Mechanism of Carbon Dioxide Adsorption in an Alkylamine-Functionalized Metal–Organic Framework
journal, April 2013
- Planas, Nora; Dzubak, Allison L.; Poloni, Roberta
- Journal of the American Chemical Society, Vol. 135, Issue 20, p. 7402-7405
Enhancement of CO 2 binding and mechanical properties upon diamine functionalization of M 2 (dobpdc) metal–organic frameworks
journal, January 2018
- Lee, Jung-Hoon; Siegelman, Rebecca L.; Maserati, Lorenzo
- Chemical Science, Vol. 9, Issue 23
Applications of metal–organic frameworks for green energy and environment: New advances in adsorptive gas separation, storage and removal
journal, July 2018
- Wang, Bin; Xie, Lin-Hua; Wang, Xiaoqing
- Green Energy & Environment, Vol. 3, Issue 3
Structure of Chemisorbed CO 2 Species in Amine-Functionalized Mesoporous Silicas Studied by Solid-State NMR and Computer Modeling
journal, December 2016
- Mafra, Luís; Čendak, Tomaž; Schneider, Sarah
- Journal of the American Chemical Society, Vol. 139, Issue 1
FTIR Study of CO2 Adsorption on Amine-Grafted SBA-15: Elucidation of Adsorbed Species
journal, May 2011
- Danon, Alon; Stair, Peter C.; Weitz, Eric
- The Journal of Physical Chemistry C, Vol. 115, Issue 23, p. 11540-11549
A diamine-grafted metal–organic framework with outstanding CO 2 capture properties and a facile coating approach for imparting exceptional moisture stability
journal, January 2019
- Kang, Minjung; Kim, Jeong Eun; Kang, Dong Won
- Journal of Materials Chemistry A, Vol. 7, Issue 14
Formation of Neutral Methylcarbamic Acid (CH 3 NHCOOH) and Methylammonium Methylcarbamate [CH 3 NH 3 + ][CH 3 NHCO 2 − ] at Low Temperature
journal, June 2008
- Bossa, Jean-Baptiste; Borget, Fabien; Duvernay, Fabrice
- The Journal of Physical Chemistry A, Vol. 112, Issue 23
Carbon Capture and Storage: How Green Can Black Be?
journal, September 2009
- Haszeldine, R. S.
- Science, Vol. 325, Issue 5948
Mechanisms of CO 2 Capture into Monoethanolamine Solution with Different CO 2 Loading during the Absorption/Desorption Processes
journal, August 2015
- Lv, Bihong; Guo, Bingsong; Zhou, Zuoming
- Environmental Science & Technology, Vol. 49, Issue 17
Studies on the solvent dependence of the carbamic acid formation from ω-(1-naphthyl)alkylamines and carbon dioxide
journal, January 2005
- Masuda, Koji; Ito, Yoshikatsu; Horiguchi, Masahiro
- Tetrahedron, Vol. 61, Issue 1
CO 2 induced phase transitions in diamine-appended metal–organic frameworks
journal, January 2015
- Vlaisavljevich, Bess; Odoh, Samuel O.; Schnell, Sondre K.
- Chemical Science, Vol. 6, Issue 9
Overcoming double-step CO 2 adsorption and minimizing water co-adsorption in bulky diamine-appended variants of Mg 2 (dobpdc)
journal, January 2018
- Milner, Phillip J.; Martell, Jeffrey D.; Siegelman, Rebecca L.
- Chemical Science, Vol. 9, Issue 1
The cost of CO2 capture and storage
journal, September 2015
- Rubin, Edward S.; Davison, John E.; Herzog, Howard J.
- International Journal of Greenhouse Gas Control, Vol. 40
Spectroscopic Characterization of Adsorbed 13 CO 2 on 3-Aminopropylsilyl-Modified SBA15 Mesoporous Silica
journal, May 2017
- Chen, Chia-Hsin; Shimon, Daphna; Lee, Jason J.
- Environmental Science & Technology, Vol. 51, Issue 11
Controlling Cooperative CO 2 Adsorption in Diamine-Appended Mg 2 (dobpdc) Metal–Organic Frameworks
journal, July 2017
- Siegelman, Rebecca L.; McDonald, Thomas M.; Gonzalez, Miguel I.
- Journal of the American Chemical Society, Vol. 139, Issue 30
CO 2 Dynamics in Pure and Mixed-Metal MOFs with Open Metal Sites
journal, October 2017
- Marti, Robert M.; Howe, Joshua D.; Morelock, Cody R.
- The Journal of Physical Chemistry C, Vol. 121, Issue 46
Degradation Pathways for Monoethanolamine in a CO 2 Capture Facility
journal, July 2003
- Strazisar, Brian R.; Anderson, Richard R.; White, Curt M.
- Energy & Fuels, Vol. 17, Issue 4
A Diaminopropane-Appended Metal–Organic Framework Enabling Efficient CO 2 Capture from Coal Flue Gas via a Mixed Adsorption Mechanism
journal, September 2017
- Milner, Phillip J.; Siegelman, Rebecca L.; Forse, Alexander C.
- Journal of the American Chemical Society, Vol. 139, Issue 38
Carbamic acid: molecular structure and IR spectra
journal, May 1999
- Khanna, R. K.; Moore, M. H.
- Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 55, Issue 5
Cooperative insertion of CO2 in diamine-appended metal-organic frameworks
journal, March 2015
- McDonald, Thomas M.; Mason, Jarad A.; Kong, Xueqian
- Nature, Vol. 519, Issue 7543
Diamine-functionalized metal–organic framework: exceptionally high CO 2 capacities from ambient air and flue gas, ultrafast CO 2 uptake rate, and adsorption mechanism
journal, January 2014
- Lee, Woo Ram; Hwang, Sang Yeon; Ryu, Dae Won
- Energy Environ. Sci., Vol. 7, Issue 2
On the potential of phase-change adsorbents for CO 2 capture by temperature swing adsorption
journal, January 2016
- Hefti, Max; Joss, Lisa; Bjelobrk, Zoran
- Faraday Discussions, Vol. 192
Methane storage in flexible metal–organic frameworks with intrinsic thermal management
journal, October 2015
- Mason, Jarad A.; Oktawiec, Julia; Taylor, Mercedes K.
- Nature, Vol. 527, Issue 7578
Selective gas adsorption and separation in metal–organic frameworks
journal, January 2009
- Li, Jian-Rong; Kuppler, Ryan J.; Zhou, Hong-Cai
- Chemical Society Reviews, Vol. 38, Issue 5, p. 1477-1504
Water Enables Efficient CO 2 Capture from Natural Gas Flue Emissions in an Oxidation-Resistant Diamine-Appended Metal–Organic Framework
journal, July 2019
- Siegelman, Rebecca L.; Milner, Phillip J.; Forse, Alexander C.
- Journal of the American Chemical Society, Vol. 141, Issue 33
The Chemistry of CO 2 Capture in an Amine-Functionalized Metal–Organic Framework under Dry and Humid Conditions
journal, August 2017
- Flaig, Robinson W.; Osborn Popp, Thomas M.; Fracaroli, Alejandro M.
- Journal of the American Chemical Society, Vol. 139, Issue 35
Chemically Modified Solid Adsorbents for CO2 Capture
journal, January 2014
- Titinchi, Salam J. J.; Piet, Marvin; Abbo, Hanna S.
- Energy Procedia, Vol. 63
Elucidating CO 2 Chemisorption in Diamine-Appended Metal–Organic Frameworks
journal, December 2018
- Forse, Alexander C.; Milner, Phillip J.; Lee, Jung-Hoon
- Journal of the American Chemical Society, Vol. 140, Issue 51
Fine-Tuning of the Carbon Dioxide Capture Capability of Diamine-Grafted Metal-Organic Framework Adsorbents Through Amine Functionalization
journal, December 2016
- Jo, Hyuna; Lee, Woo Ram; Kim, Nam Woo
- ChemSusChem, Vol. 10, Issue 3
Adsorption and Activation of CO2 by Amine-Modified Nanoporous Materials Studied by Solid-State NMR and 13CO2 Adsorption
journal, March 2011
- Pinto, Moisés L.; Mafra, Luís; Guil, José M.
- Chemistry of Materials, Vol. 23, Issue 6, p. 1387-1395