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Title: Cooperative adsorption of carbon disulfide in diamine-appended metal–organic frameworks

Abstract

Over one million tons of CS2 are produced annually, and emissions of this volatile and toxic liquid, known to generate acid rain, remain poorly controlled. As such, materials capable of reversibly capturing this commodity chemical in an energy-efficient manner are of interest. Recently, we detailed diamine-appended metal–organic frameworks capable of selectively capturing CO2 through a cooperative insertion mechanism that promotes efficient adsorption–desorption cycling. We therefore sought to explore the ability of these materials to capture CS2 through a similar mechanism. Employing crystallography, spectroscopy, and gas adsorption analysis, we demonstrate that CS2 is indeed cooperatively adsorbed in N,N-dimethylethylenediamine-appended M2(dobpdc) (M = Mg, Mn, Zn; dobpdc4- = 4,4'-dioxidobiphenyl-3,3'-dicarboxylate), via the formation of electrostatically paired ammonium dithiocarbamate chains. In the weakly thiophilic Mg congener, chemisorption is cleanly reversible with mild thermal input. Finally, this work demonstrates that the cooperative insertion mechanism can be generalized to other high-impact target molecules.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3];  [2];  [4];  [4];  [4]; ORCiD logo [5];  [4];  [4];  [4]; ORCiD logo [4]; ORCiD logo [6]
  1. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
  2. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Sciences Division
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
  4. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry
  5. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
  6. Univ. of California, Berkeley, CA (United States). Dept. of Chemical and Biomolecular Engineering
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1493273
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 9; Journal Issue: 1; Journal ID: ISSN 2041-1723
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE

Citation Formats

McGuirk, C. Michael, Siegelman, Rebecca L., Drisdell, Walter S., Runčevski, Tomče, Milner, Phillip J., Oktawiec, Julia, Wan, Liwen F., Su, Gregory M., Jiang, Henry Z. H., Reed, Douglas A., Gonzalez, Miguel I., Prendergast, David, and Long, Jeffrey R. Cooperative adsorption of carbon disulfide in diamine-appended metal–organic frameworks. United States: N. p., 2018. Web. doi:10.1038/s41467-018-07458-6.
McGuirk, C. Michael, Siegelman, Rebecca L., Drisdell, Walter S., Runčevski, Tomče, Milner, Phillip J., Oktawiec, Julia, Wan, Liwen F., Su, Gregory M., Jiang, Henry Z. H., Reed, Douglas A., Gonzalez, Miguel I., Prendergast, David, & Long, Jeffrey R. Cooperative adsorption of carbon disulfide in diamine-appended metal–organic frameworks. United States. doi:10.1038/s41467-018-07458-6.
McGuirk, C. Michael, Siegelman, Rebecca L., Drisdell, Walter S., Runčevski, Tomče, Milner, Phillip J., Oktawiec, Julia, Wan, Liwen F., Su, Gregory M., Jiang, Henry Z. H., Reed, Douglas A., Gonzalez, Miguel I., Prendergast, David, and Long, Jeffrey R. Mon . "Cooperative adsorption of carbon disulfide in diamine-appended metal–organic frameworks". United States. doi:10.1038/s41467-018-07458-6. https://www.osti.gov/servlets/purl/1493273.
@article{osti_1493273,
title = {Cooperative adsorption of carbon disulfide in diamine-appended metal–organic frameworks},
author = {McGuirk, C. Michael and Siegelman, Rebecca L. and Drisdell, Walter S. and Runčevski, Tomče and Milner, Phillip J. and Oktawiec, Julia and Wan, Liwen F. and Su, Gregory M. and Jiang, Henry Z. H. and Reed, Douglas A. and Gonzalez, Miguel I. and Prendergast, David and Long, Jeffrey R.},
abstractNote = {Over one million tons of CS2 are produced annually, and emissions of this volatile and toxic liquid, known to generate acid rain, remain poorly controlled. As such, materials capable of reversibly capturing this commodity chemical in an energy-efficient manner are of interest. Recently, we detailed diamine-appended metal–organic frameworks capable of selectively capturing CO2 through a cooperative insertion mechanism that promotes efficient adsorption–desorption cycling. We therefore sought to explore the ability of these materials to capture CS2 through a similar mechanism. Employing crystallography, spectroscopy, and gas adsorption analysis, we demonstrate that CS2 is indeed cooperatively adsorbed in N,N-dimethylethylenediamine-appended M2(dobpdc) (M = Mg, Mn, Zn; dobpdc4- = 4,4'-dioxidobiphenyl-3,3'-dicarboxylate), via the formation of electrostatically paired ammonium dithiocarbamate chains. In the weakly thiophilic Mg congener, chemisorption is cleanly reversible with mild thermal input. Finally, this work demonstrates that the cooperative insertion mechanism can be generalized to other high-impact target molecules.},
doi = {10.1038/s41467-018-07458-6},
journal = {Nature Communications},
number = 1,
volume = 9,
place = {United States},
year = {2018},
month = {12}
}

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Cited by: 6 works
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    Works referencing / citing this record:

    Cobalt substitution in a flexible metal–organic framework: modulating a soft paddle-wheel unit for tunable gate-opening adsorption
    journal, January 2019

    • Zhu, Jiaxing; Chen, Junye; Qiu, Tianze
    • Dalton Transactions, Vol. 48, Issue 21
    • DOI: 10.1039/c9dt00115h

    637. The stability of transition-metal complexes
    journal, January 1953

    • Irving, H.; Williams, R. J. P.
    • Journal of the Chemical Society (Resumed), Vol. 0, Issue 0, p. 3192-3210
    • DOI: 10.1039/jr9530003192

    Ethane/Ethene Separation Turned on Its Head: Selective Ethane Adsorption on the Metal−Organic Framework ZIF-7 through a Gate-Opening Mechanism
    journal, December 2010

    • Gücüyener, Canan; van den Bergh, Johan; Gascon, Jorge
    • Journal of the American Chemical Society, Vol. 132, Issue 50
    • DOI: 10.1021/ja1089765

    Evolution of a new enzyme for carbon disulphide conversion by an acidothermophilic archaeon
    journal, October 2011

    • Smeulders, Marjan J.; Barends, Thomas R. M.; Pol, Arjan
    • Nature, Vol. 478, Issue 7369
    • DOI: 10.1038/nature10464

    Carbon Dioxide Capture in Metal–Organic Frameworks
    journal, September 2011

    • Sumida, Kenji; Rogow, David L.; Mason, Jarad A.
    • Chemical Reviews, Vol. 112, Issue 2, p. 724-781
    • DOI: 10.1021/cr2003272

    Porous Coordination-Polymer Crystals with Gated Channels Specific for Supercritical Gases
    journal, January 2003

    • Kitaura, Ryo; Seki, Kenji; Akiyama, George
    • Angewandte Chemie International Edition, Vol. 42, Issue 4
    • DOI: 10.1002/anie.200390130

    Broadly Hysteretic H 2 Adsorption in the Microporous Metal−Organic Framework Co(1,4-benzenedipyrazolate)
    journal, June 2008

    • Choi, Hye Jin; Dincă, Mircea; Long, Jeffrey R.
    • Journal of the American Chemical Society, Vol. 130, Issue 25
    • DOI: 10.1021/ja8024092

    The Chemistry and Applications of Metal-Organic Frameworks
    journal, August 2013

    • Furukawa, H.; Cordova, K. E.; O'Keeffe, M.
    • Science, Vol. 341, Issue 6149, p. 1230444-1230444
    • DOI: 10.1126/science.1230444

    Crystallographic report: (2,9-Dimethyl-1,10-phenanthroline)bis-(N,N-pyrrolidinedithiocarbamato)zinc(II) chloroform hemihydrate
    journal, January 2003

    • Sing Lai, Chian; Tiekink, Edward R. T.
    • Applied Organometallic Chemistry, Vol. 17, Issue 4
    • DOI: 10.1002/aoc.422

    Adsorption and Its Mechanism of CS 2 on Ion-Exchanged Zeolites Y
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    • Chen, Xi; Shen, Ben-xian; Sun, Hui
    • Industrial & Engineering Chemistry Research, Vol. 56, Issue 22
    • DOI: 10.1021/acs.iecr.7b00245

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    journal, June 1991

    • Tyndall, Geoffrey S.; Ravishankara, A. R.
    • International Journal of Chemical Kinetics, Vol. 23, Issue 6
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    journal, June 2009

    • Ohba, Masaaki; Yoneda, Ko; Agustí, Gloria
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    • DOI: 10.1002/anie.200806039

    Atmospheric oxidation of carbon disulfide (CS2)
    journal, February 2017


    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
    • DOI: 10.1021/jacs.7b05858

    Absorption of CO 2 and CS 2 into the Hofmann-Type Porous Coordination Polymer: Electrostatic versus Dispersion Interactions
    journal, March 2013

    • Deshmukh, Milind Madhusudan; Ohba, Masaaki; Kitagawa, Susumu
    • Journal of the American Chemical Society, Vol. 135, Issue 12
    • DOI: 10.1021/ja400537f

    Methane Storage in Metal–Organic Frameworks: Current Records, Surprise Findings, and Challenges
    journal, July 2013

    • Peng, Yang; Krungleviciute, Vaiva; Eryazici, Ibrahim
    • Journal of the American Chemical Society, Vol. 135, Issue 32, p. 11887-11894
    • DOI: 10.1021/ja4045289

    Soft porous crystals
    journal, November 2009

    • Horike, Satoshi; Shimomura, Satoru; Kitagawa, Susumu
    • Nature Chemistry, Vol. 1, Issue 9, p. 695-704
    • DOI: 10.1038/nchem.444

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    • McGuirk, C. Michael; Siegelman, Rebecca L.; Drisdell, Walter S.
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    Application of a High-Throughput Analyzer in Evaluating Solid Adsorbents for Post-Combustion Carbon Capture via Multicomponent Adsorption of CO 2 , N 2 , and H 2 O
    journal, April 2015

    • Mason, Jarad A.; McDonald, Thomas M.; Bae, Tae-Hyun
    • Journal of the American Chemical Society, Vol. 137, Issue 14
    • DOI: 10.1021/jacs.5b00838

    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
    • DOI: 10.1038/nature14327

    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
    • DOI: 10.1038/nature15732

    Crystallographic report:(2,2′-Bipyridyl)bis(ethanoldithiocarbamato)zinc(II)
    journal, January 2004

    • Saravanan, M.; Ramalingam, K.; Bocelli, G.
    • Applied Organometallic Chemistry, Vol. 18, Issue 2
    • DOI: 10.1002/aoc.525

    Reactions of carbon disulfide with N-nucleophiles
    journal, June 2007


    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
    • DOI: 10.1021/jacs.7b07612

    Metal Ion Binding to Octakis(dimethylamino)porphyrazine:  Core Coordination of Mn(III) and Peripheral Coordination of Pd(II)
    journal, June 1998

    • Goldberg, David P.; Montalban, Antonio Garrido; White, Andrew J. P.
    • Inorganic Chemistry, Vol. 37, Issue 12
    • DOI: 10.1021/ic970624e

    Introduction to Metal–Organic Frameworks
    journal, September 2011

    • Zhou, Hong-Cai; Long, Jeffrey R.; Yaghi, Omar M.
    • Chemical Reviews, Vol. 112, Issue 2, p. 673-674
    • DOI: 10.1021/cr300014x

    Enthalpies and Entropies of Adsorption on Well-Defined Oxide Surfaces: Experimental Measurements
    journal, December 2012

    • Campbell, Charles T.; Sellers, Jason R. V.
    • Chemical Reviews, Vol. 113, Issue 6
    • DOI: 10.1021/cr300329s

    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
    • DOI: 10.1039/b802426j

    Cobalt substitution in a flexible metal–organic framework: modulating a soft paddle-wheel unit for tunable gate-opening adsorption
    journal, January 2019

    • Zhu, Jiaxing; Chen, Junye; Qiu, Tianze
    • Dalton Transactions, Vol. 48, Issue 21
    • DOI: 10.1039/c9dt00115h