Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks

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.

doi:10.1002/ange.201915561

Title: Cooperative Carbon Dioxide Adsorption in Alcoholamine- and Alkoxyalkylamine-Functionalized Metal–Organic Frameworks

Journal Article · 26 December 2019 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.201915561 · OSTI ID:1634073

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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

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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE National Energy Technology Laboratory (NETL); National Institutes of Health (NIH)

Grant/Contract Number:: AC02-05CH11231; SC0019992; FWP-00006194; F32GM120799

OSTI ID:: 1634073

Alternate ID(s):: OSTI ID: 1597159

Journal Information:: Angewandte Chemie, Vol. 132, Issue 44; ISSN 0044-8249

Publisher:: German Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (30)

The Mechanism of Carbon Dioxide Adsorption in an Alkylamine-Functionalized Metal–Organic Framework Planas, Nora; Dzubak, Allison L.; Poloni, Roberta Journal of the American Chemical Society, Vol. 135, Issue 20, p. 7402-7405 https://doi.org/10.1021/ja4004766	journal	April 2013
Enhancement of CO ₂ binding and mechanical properties upon diamine functionalization of M ₂ (dobpdc) metal–organic frameworks Lee, Jung-Hoon; Siegelman, Rebecca L.; Maserati, Lorenzo Chemical Science, Vol. 9, Issue 23 https://doi.org/10.1039/C7SC05217K	journal	January 2018
Applications of metal–organic frameworks for green energy and environment: New advances in adsorptive gas separation, storage and removal Wang, Bin; Xie, Lin-Hua; Wang, Xiaoqing Green Energy & Environment, Vol. 3, Issue 3 https://doi.org/10.1016/j.gee.2018.03.001	journal	July 2018
Structure of Chemisorbed CO ₂ Species in Amine-Functionalized Mesoporous Silicas Studied by Solid-State NMR and Computer Modeling Mafra, Luís; Čendak, Tomaž; Schneider, Sarah Journal of the American Chemical Society, Vol. 139, Issue 1 https://doi.org/10.1021/jacs.6b11081	journal	December 2016
FTIR Study of CO₂ Adsorption on Amine-Grafted SBA-15: Elucidation of Adsorbed Species Danon, Alon; Stair, Peter C.; Weitz, Eric The Journal of Physical Chemistry C, Vol. 115, Issue 23, p. 11540-11549 https://doi.org/10.1021/jp200914v	journal	May 2011
A diamine-grafted metal–organic framework with outstanding CO ₂ capture properties and a facile coating approach for imparting exceptional moisture stability Kang, Minjung; Kim, Jeong Eun; Kang, Dong Won Journal of Materials Chemistry A, Vol. 7, Issue 14 https://doi.org/10.1039/C8TA07965J	journal	January 2019
Formation of Neutral Methylcarbamic Acid (CH ₃ NHCOOH) and Methylammonium Methylcarbamate [CH ₃ NH ₃ ⁺ ][CH ₃ NHCO ₂ ⁻ ] at Low Temperature Bossa, Jean-Baptiste; Borget, Fabien; Duvernay, Fabrice The Journal of Physical Chemistry A, Vol. 112, Issue 23 https://doi.org/10.1021/jp800723c	journal	June 2008
Carbon Capture and Storage: How Green Can Black Be? Haszeldine, R. S. Science, Vol. 325, Issue 5948 https://doi.org/10.1126/science.1172246	journal	September 2009
Mechanisms of CO ₂ Capture into Monoethanolamine Solution with Different CO ₂ Loading during the Absorption/Desorption Processes Lv, Bihong; Guo, Bingsong; Zhou, Zuoming Environmental Science & Technology, Vol. 49, Issue 17 https://doi.org/10.1021/acs.est.5b02356	journal	August 2015
Studies on the solvent dependence of the carbamic acid formation from ω-(1-naphthyl)alkylamines and carbon dioxide Masuda, Koji; Ito, Yoshikatsu; Horiguchi, Masahiro Tetrahedron, Vol. 61, Issue 1 https://doi.org/10.1016/j.tet.2004.10.033	journal	January 2005
CO ₂ induced phase transitions in diamine-appended metal–organic frameworks Vlaisavljevich, Bess; Odoh, Samuel O.; Schnell, Sondre K. Chemical Science, Vol. 6, Issue 9 https://doi.org/10.1039/C5SC01828E	journal	January 2015
Overcoming double-step CO ₂ adsorption and minimizing water co-adsorption in bulky diamine-appended variants of Mg ₂ (dobpdc) Milner, Phillip J.; Martell, Jeffrey D.; Siegelman, Rebecca L. Chemical Science, Vol. 9, Issue 1 https://doi.org/10.1039/C7SC04266C	journal	January 2018
The cost of CO2 capture and storage Rubin, Edward S.; Davison, John E.; Herzog, Howard J. International Journal of Greenhouse Gas Control, Vol. 40 https://doi.org/10.1016/j.ijggc.2015.05.018	journal	September 2015
Spectroscopic Characterization of Adsorbed ¹³ CO ₂ on 3-Aminopropylsilyl-Modified SBA15 Mesoporous Silica Chen, Chia-Hsin; Shimon, Daphna; Lee, Jason J. Environmental Science & Technology, Vol. 51, Issue 11 https://doi.org/10.1021/acs.est.6b06605	journal	May 2017
Controlling Cooperative CO ₂ Adsorption in Diamine-Appended Mg ₂ (dobpdc) Metal–Organic Frameworks Siegelman, Rebecca L.; McDonald, Thomas M.; Gonzalez, Miguel I. Journal of the American Chemical Society, Vol. 139, Issue 30 https://doi.org/10.1021/jacs.7b05858	journal	July 2017
CO ₂ Dynamics in Pure and Mixed-Metal MOFs with Open Metal Sites Marti, Robert M.; Howe, Joshua D.; Morelock, Cody R. The Journal of Physical Chemistry C, Vol. 121, Issue 46 https://doi.org/10.1021/acs.jpcc.7b07179	journal	October 2017
Degradation Pathways for Monoethanolamine in a CO ₂ Capture Facility Strazisar, Brian R.; Anderson, Richard R.; White, Curt M. Energy & Fuels, Vol. 17, Issue 4 https://doi.org/10.1021/ef020272i	journal	July 2003
A Diaminopropane-Appended Metal–Organic Framework Enabling Efficient CO ₂ Capture from Coal Flue Gas via a Mixed Adsorption Mechanism Milner, Phillip J.; Siegelman, Rebecca L.; Forse, Alexander C. Journal of the American Chemical Society, Vol. 139, Issue 38 https://doi.org/10.1021/jacs.7b07612	journal	September 2017
Carbamic acid: molecular structure and IR spectra Khanna, R. K.; Moore, M. H. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 55, Issue 5 https://doi.org/10.1016/S1386-1425(98)00228-5	journal	May 1999
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
Diamine-functionalized metal–organic framework: exceptionally high CO ₂ capacities from ambient air and flue gas, ultrafast CO ₂ uptake rate, and adsorption mechanism Lee, Woo Ram; Hwang, Sang Yeon; Ryu, Dae Won Energy Environ. Sci., Vol. 7, Issue 2 https://doi.org/10.1039/C3EE42328J	journal	January 2014
On the potential of phase-change adsorbents for CO ₂ capture by temperature swing adsorption Hefti, Max; Joss, Lisa; Bjelobrk, Zoran Faraday Discussions, Vol. 192 https://doi.org/10.1039/C6FD00040A	journal	January 2016
Methane storage in flexible metal–organic frameworks with intrinsic thermal management Mason, Jarad A.; Oktawiec, Julia; Taylor, Mercedes K. Nature, Vol. 527, Issue 7578 https://doi.org/10.1038/nature15732	journal	October 2015
Selective gas adsorption and separation in metal–organic frameworks Li, Jian-Rong; Kuppler, Ryan J.; Zhou, Hong-Cai Chemical Society Reviews, Vol. 38, Issue 5, p. 1477-1504 https://doi.org/10.1039/b802426j	journal	January 2009
Water Enables Efficient CO ₂ Capture from Natural Gas Flue Emissions in an Oxidation-Resistant Diamine-Appended Metal–Organic Framework Siegelman, Rebecca L.; Milner, Phillip J.; Forse, Alexander C. Journal of the American Chemical Society, Vol. 141, Issue 33 https://doi.org/10.1021/jacs.9b05567	journal	July 2019
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
Chemically Modified Solid Adsorbents for CO2 Capture Titinchi, Salam J. J.; Piet, Marvin; Abbo, Hanna S. Energy Procedia, Vol. 63 https://doi.org/10.1016/j.egypro.2015.12.337	journal	January 2014
Elucidating CO ₂ Chemisorption in Diamine-Appended Metal–Organic Frameworks Forse, Alexander C.; Milner, Phillip J.; Lee, Jung-Hoon Journal of the American Chemical Society, Vol. 140, Issue 51 https://doi.org/10.1021/jacs.8b10203	journal	December 2018
Fine-Tuning of the Carbon Dioxide Capture Capability of Diamine-Grafted Metal-Organic Framework Adsorbents Through Amine Functionalization Jo, Hyuna; Lee, Woo Ram; Kim, Nam Woo ChemSusChem, Vol. 10, Issue 3 https://doi.org/10.1002/cssc.201601203	journal	December 2016
Adsorption and Activation of CO₂ by Amine-Modified Nanoporous Materials Studied by Solid-State NMR and ¹³CO₂ Adsorption Pinto, Moisés L.; Mafra, Luís; Guil, José M. Chemistry of Materials, Vol. 23, Issue 6, p. 1387-1395 https://doi.org/10.1021/cm1029563	journal	March 2011

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