Fluoroarene Separations in Metal-Organic Frameworks with Two Proximal Mg2+ Coordination Sites

Zick, Mary E.; Lee, Jung-Hoon; Gonzalez, Miguel I.; Velasquez, Ever O.; Uliana, Adam A.; Kim, Jaehwan; Long, Jeffrey R.; Milner, Phillip J.

doi:10.1021/jacs.0c11530

Title: Fluoroarene Separations in Metal-Organic Frameworks with Two Proximal Mg²⁺ Coordination Sites

Journal Article · Mon Jan 25 00:00:00 EST 2021 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.0c11530· OSTI ID:1842998

Zick, Mary E. ^[1];

^[2]; Gonzalez, Miguel I. ^[1]; Velasquez, Ever O. ^[3]; Uliana, Adam A. ^[3]; Kim, Jaehwan ^[1];

^[4];

^[1]

Cornell Univ., Ithaca, NY (United States)
Korea Institute of Science and Technology (KIST), Seoul (Republic of Korea)
Univ. of California, Berkeley, CA (United States)
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Fluoroarenes which are widely used in medicinal, agricultural, and materials chemistry, and yet their production remains a critical challenge in organic synthesis. Indeed, the nearly identical physical properties of these vital building blocks hinders their purification by traditional methods, such as flash chromatography or distillation. As a result, the Balz-Schiemann reaction is currently employed to prepare fluoroarenes instead of more atom-economical C-H fluorination reactions, which produce inseparable mixtures of regioisomers. Herein, we propose an alternative solution to this problem: the purification of mixtures of fluoroarenes using metal-organic frameworks (MOFs). Specifically, we demonstrate that controlling the interaction of fluoroarenes with adjacent coordinatively unsaturated Mg²⁺ centers within a MOF enables the separation of fluoroarene mixtures with unparalleled selectivities. Liquid-phase multicomponent equilibrium adsorption data and breakthrough measurements coupled with van der Waals-corrected density functional theory calculations reveal that the materials Mg₂(dobdc) (dobdc^4- = 2,5-dioxidobenzene-1,4-dicarboxylate) and Mg₂(m-dobdc) (m-dobdc^4- = 2,4-dioxidobenzene-1,5-dicarboxylate) are capable of separating the difluorobenzene isomers from one another. Additionally, these frameworks facilitate the separations of fluoroanisoles, fluorotoluenes, and fluorochlorobenzenes. In addition to enabling currently unfeasible separations for the production of fluoroarenes, our results suggest that carefully controlling the interaction of isomers with not one but two strong binding sites within a MOF provides a general strategy for achieving challenging liquid-phase 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); National Institutes of Health (NIH); Korean Institute of Science and Technology (KIST)

Grant/Contract Number:: AC02-05CH11231; F32GM120799; R35GM138165; 2E30460; KSC-2019-CRE-0149; DMR-1719875; CHE-1531632

OSTI ID:: 1842998

Journal Information:: Journal of the American Chemical Society, Vol. 143, Issue 4; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (87)

A Chemically Functionalizable Nanoporous Material [Cu₃(TMA)₂(H₂O)₃]_n Chui, Stephen S.-Y.; Lo, Samuel M.-F.; Charmant, Jonathan P. H. Science, Vol. 283, Issue 5405, p. 1148-1150 https://doi.org/10.1126/science.283.5405.1148	journal	February 1999
Silica-MOF Composites as a Stationary Phase in Liquid Chromatography Ameloot, Rob; Liekens, Anuschka; Alaerts, Luc European Journal of Inorganic Chemistry, Vol. 2010, Issue 24 https://doi.org/10.1002/ejic.201000494	journal	June 2010
Organometallic chemistry using partially fluorinated benzenes Pike, Sebastian D.; Crimmin, Mark R.; Chaplin, Adrian B. Chemical Communications, Vol. 53, Issue 26 https://doi.org/10.1039/C6CC09575E	journal	January 2017
Synthesis, structure, and spectroscopy of pseudotetrahedral CoIIN3(SR) complexes. Active site approximations to the cobalt(II)-substituted type 1 copper proteins Thompson, Jeffery S.; Sorrell, Theophilus; Marks, Tobin J. Journal of the American Chemical Society, Vol. 101, Issue 15 https://doi.org/10.1021/ja00509a027	journal	July 1979
The Coordination Chemistry of the CF Unit in Fluorocarbons Plenio, Herbert Chemical Reviews, Vol. 97, Issue 8 https://doi.org/10.1021/cr970465g	journal	December 1997
Highly Lewis acidic cationic alkaline earth metal complexes Pahl, Jürgen; Brand, Steffen; Elsen, Holger Chemical Communications, Vol. 54, Issue 63 https://doi.org/10.1039/C8CC04083D	journal	January 2018
A functional zeolite analogue assembled from metalloporphyrins Kosal, Margaret E.; Chou, Jun-Hong; Wilson, Scott R. Nature Materials, Vol. 1, Issue 2 https://doi.org/10.1038/nmat730	journal	September 2002
Liquid Phase Separation of Polyaromatics on [Cu ₂ (BDC) ₂ (dabco)] Maes, Michael; Schouteden, Stijn; Hirai, Kenji Langmuir, Vol. 27, Issue 15 https://doi.org/10.1021/la2018049	journal	June 2011
Palladium-catalysed electrophilic aromatic C–H fluorination Yamamoto, Kumiko; Li, Jiakun; Garber, Jeffrey A. O. Nature, Vol. 554, Issue 7693 https://doi.org/10.1038/nature25749	journal	February 2018
Selective Adsorption and Separation of ortho -Substituted Alkylaromatics with the Microporous Aluminum Terephthalate MIL-53 Alaerts, Luc; Maes, Michael; Giebeler, Lars Journal of the American Chemical Society, Vol. 130, Issue 43 https://doi.org/10.1021/ja802761z	journal	October 2008
M₂(m-dobdc) (M = Mg, Mn, Fe, Co, Ni) Metal–Organic Frameworks Exhibiting Increased Charge Density and Enhanced H₂ Binding at the Open Metal Sites Kapelewski, Matthew T.; Geier, Stephen J.; Hudson, Matthew R. Journal of the American Chemical Society, Vol. 136, Issue 34, p. 12119-12129 https://doi.org/10.1021/ja506230r	journal	August 2014
Fluorination methods for drug discovery and development Richardson, Paul Expert Opinion on Drug Discovery, Vol. 11, Issue 10 https://doi.org/10.1080/17460441.2016.1223037	journal	August 2016
The Modular Synthesis of Functional Porous Coordination Networks Kawano, Masaki; Kawamichi, Takehide; Haneda, Tsuyoshi Journal of the American Chemical Society, Vol. 129, Issue 50, p. 15418-15419 https://doi.org/10.1021/ja0752540	journal	December 2007
Overview on the history of organofluorine chemistry from the viewpoint of material industry Okazoe, Takashi Proceedings of the Japan Academy, Series B, Vol. 85, Issue 8 https://doi.org/10.2183/pjab.85.276	journal	January 2009
An In Situ High-Temperature Single-Crystal Investigation of a Dehydrated Metal-Organic Framework Compound and Field-Induced Magnetization of One-Dimensional Metal-Oxygen Chains Dietzel, Pascal D. C.; Morita, Yusuke; Blom, Richard Angewandte Chemie International Edition, Vol. 44, Issue 39, p. 6354-6358 https://doi.org/10.1002/anie.200501508	journal	October 2005
Introduction of Fluorine and Fluorine-Containing Functional Groups Liang, Theresa; Neumann, Constanze N.; Ritter, Tobias Angewandte Chemie International Edition, Vol. 52, Issue 32 https://doi.org/10.1002/anie.201206566	journal	July 2013
New Directions in C–H Fluorination Cheng, Qiang; Ritter, Tobias Trends in Chemistry, Vol. 1, Issue 5 https://doi.org/10.1016/j.trechm.2019.04.001	journal	August 2019
Metal-organic frameworks in chromatography Yusuf, Kareem; Aqel, Ahmad; ALOthman, Zeid Journal of Chromatography A, Vol. 1348 https://doi.org/10.1016/j.chroma.2014.04.095	journal	June 2014
Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides Furuya, Takeru; Klein, Johannes; Ritter, Tobias Synthesis, Vol. 2010, Issue 11 https://doi.org/10.1055/s-0029-1218742	journal	April 2010
An extremely stable open-framework metal–organic polymer with expandable structure and selective adsorption capabilityElectronic supplementary information (ESI) available: Figs. S1 and S2: views of propanol inclusion structure. See http://www.rsc.org/suppdata/cc/b2/b200213b/ Lu, Jack Y.; Babb, Amy M. Chemical Communications, Issue 13 https://doi.org/10.1039/b200213b	journal	May 2002
Selective binding and removal of guests in a microporous metal–organic framework Yaghi, O. M.; Li, Guangming; Li, Hailian Nature, Vol. 378, Issue 6558, p. 703-706 https://doi.org/10.1038/378703a0	journal	December 1995
Recent advances in gas storage and separation using metal–organic frameworks Li, Hao; Wang, Kecheng; Sun, Yujia Materials Today, Vol. 21, Issue 2 https://doi.org/10.1016/j.mattod.2017.07.006	journal	March 2018
Metal–Organic Frameworks for Analytical Chemistry: From Sample Collection to Chromatographic Separation Gu, Zhi-Yuan; Yang, Cheng-Xiong; Chang, Na Accounts of Chemical Research, Vol. 45, Issue 5 https://doi.org/10.1021/ar2002599	journal	January 2012
Facile synthesis of nanocrystals of a microporous metal–organic framework by an ultrasonic method and selective sensing of organoamines Qiu, Ling-Guang; Li, Zong-Qun; Wu, Yun Chemical Communications, Issue 31 https://doi.org/10.1039/b804126a	journal	January 2008
Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas Zhou, Yu; Wang, Jiang; Gu, Zhanni Chemical Reviews, Vol. 116, Issue 2 https://doi.org/10.1021/acs.chemrev.5b00392	journal	January 2016
CD-MOF: A Versatile Separation Medium Hartlieb, Karel J.; Holcroft, James M.; Moghadam, Peyman Z. Journal of the American Chemical Society, Vol. 138, Issue 7 https://doi.org/10.1021/jacs.5b12860	journal	February 2016
Pd-Catalyzed Nucleophilic Fluorination of Aryl Bromides Lee, Hong Geun; Milner, Phillip J.; Buchwald, Stephen L. Journal of the American Chemical Society, Vol. 136, Issue 10 https://doi.org/10.1021/ja5009739	journal	February 2014
Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C–F Bond Activation To Access Fluorinated Building Blocks Ahrens, Theresia; Kohlmann, Johannes; Ahrens, Mike Chemical Reviews, Vol. 115, Issue 2 https://doi.org/10.1021/cr500257c	journal	August 2014
Modern Carbon–Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis Campbell, Michael G.; Ritter, Tobias Chemical Reviews, Vol. 115, Issue 2 https://doi.org/10.1021/cr500366b	journal	August 2014
Structure of the Decamethyl Titanocene Cation, a Metallocene with Two Agostic C−H Bonds, and Its Interaction with Fluorocarbons Bouwkamp, Marco W.; de Wolf, Jeanette; del Hierro Morales, Isabel Journal of the American Chemical Society, Vol. 124, Issue 44 https://doi.org/10.1021/ja027617w	journal	October 2002
The Coordination Chemistry of Fluorine in Fluorocarbons Plenio, Herbert ChemBioChem, Vol. 5, Issue 5 https://doi.org/10.1002/cbic.200300752	journal	April 2004
The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection Jeschke, Peter ChemBioChem, Vol. 5, Issue 5 https://doi.org/10.1002/cbic.200300833	journal	April 2004
Structural characterization of framework–gas interactions in the metal–organic framework Co ₂ (dobdc) by in situ single-crystal X-ray diffraction Gonzalez, Miguel I.; Mason, Jarad A.; Bloch, Eric D. Chemical Science, Vol. 8, Issue 6 https://doi.org/10.1039/C7SC00449D	journal	January 2017
Selectivity of C–H Activation and Competition between C–H and C–F Bond Activation at Fluorocarbons Eisenstein, Odile; Milani, Jessica; Perutz, Robin N. Chemical Reviews, Vol. 117, Issue 13 https://doi.org/10.1021/acs.chemrev.7b00163	journal	June 2017
Reduction of Terphenyl Co(II) Halide Derivatives in the Presence of Arenes: Insertion of Co(I) into a C–F Bond Lei, Hao; Fettinger, James C.; Power, Philip P. Inorganic Chemistry, Vol. 51, Issue 3 https://doi.org/10.1021/ic202116s	journal	January 2012
Recent advances in C–H fluorination Lin, Aijun; Huehls, C. Bryan; Yang, Jiong Org. Chem. Front., Vol. 1, Issue 4 https://doi.org/10.1039/C4QO00020J	journal	January 2014
Recent advances in metal-organic frameworks and covalent organic frameworks for sample preparation and chromatographic analysis Wang, Xuan; Ye, Nengsheng ELECTROPHORESIS, Vol. 38, Issue 24 https://doi.org/10.1002/elps.201700248	journal	September 2017
Dramatic Tuning of Carbon Dioxide Uptake via Metal Substitution in a Coordination Polymer with Cylindrical Pores Caskey, Stephen R.; Wong-Foy, Antek G.; Matzger, Adam J. Journal of the American Chemical Society, Vol. 130, Issue 33, p. 10870-10871 https://doi.org/10.1021/ja8036096	journal	August 2008
Fluorine in Pharmaceuticals: Looking Beyond Intuition Muller, K.; Faeh, C.; Diederich, F. Science, Vol. 317, Issue 5846 https://doi.org/10.1126/science.1131943	journal	September 2007
Selective Guest Binding by Tailored Channels in a 3-D Porous Zinc(II)−Benzenetricarboxylate Network Yaghi, O. M.; Davis, Charles E.; Li, Guangming Journal of the American Chemical Society, Vol. 119, Issue 12, p. 2861-2868 https://doi.org/10.1021/ja9639473	journal	March 1997
Networked molecular cages as crystalline sponges for fullerenes and other guests Inokuma, Yasuhide; Arai, Tatsuhiko; Fujita, Makoto Nature Chemistry, Vol. 2, Issue 9 https://doi.org/10.1038/nchem.742	journal	July 2010
Adsorption and Separation of Reactive Aromatic Isomers and Generation and Stabilization of Their Radicals within Cadmium(II)−Triazole Metal−Organic Confined Space in a Single-Crystal-to-Single-Crystal Fashion Liu, Qi-Kui; Ma, Jian-Ping; Dong, Yu-Bin Journal of the American Chemical Society, Vol. 132, Issue 20 https://doi.org/10.1021/ja101807c	journal	May 2010
Selective Adsorption and Separation of Xylene Isomers and Ethylbenzene with the Microporous Vanadium(IV) Terephthalate MIL-47 Alaerts, Luc; Kirschhock, Christine E. A.; Maes, Michael Angewandte Chemie International Edition, Vol. 46, Issue 23 https://doi.org/10.1002/anie.200700056	journal	June 2007
A Structurally Characterized Cobalt(I) σ‐Alkane Complex Boyd, Timothy M.; Tegner, Bengt E.; Tizzard, Graham J. Angewandte Chemie International Edition, Vol. 59, Issue 15 https://doi.org/10.1002/anie.201914940	journal	February 2020
Rapid Synthesis of Aryl Fluorides in Continuous Flow through the Balz-Schiemann Reaction Park, Nathaniel H.; Senter, Timothy J.; Buchwald, Stephen L. Angewandte Chemie International Edition, Vol. 55, Issue 39 https://doi.org/10.1002/anie.201606601	journal	August 2016
19F NMR Spectra and Structures of Halogenated Porphyrins Birnbaum, Eva R.; Hodge, Julia A.; Grinstaff, Mark W. Inorganic Chemistry, Vol. 34, Issue 14 https://doi.org/10.1021/ic00118a010	journal	July 1995
Coordination chemistry of halocarbons Kulawiec, Robert J.; Crabtree, Robert H. Coordination Chemistry Reviews, Vol. 99 https://doi.org/10.1016/0010-8545(90)80061-W	journal	March 1990
Naked (C ₅ Me ₅ ) ₂ M Cations (M = Sc, Ti, and V) and Their Fluoroarene Complexes Bouwkamp, Marco W.; Budzelaar, Peter H. M.; Gercama, Jeroen Journal of the American Chemical Society, Vol. 127, Issue 41 https://doi.org/10.1021/ja054544i	journal	October 2005
Separation of Styrene and Ethylbenzene on Metal−Organic Frameworks: Analogous Structures with Different Adsorption Mechanisms Maes, Michael; Vermoortele, Frederik; Alaerts, Luc Journal of the American Chemical Society, Vol. 132, Issue 43 https://doi.org/10.1021/ja106142x	journal	November 2010
Chromatographic Resolution of Closely Related Species in Pharmaceutical Chemistry: Dehalogenation Impurities and Mixtures of Halogen Isomers Regalado, Erik L.; Zhuang, Ping; Chen, Yadan Analytical Chemistry, Vol. 86, Issue 1 https://doi.org/10.1021/ac403376h	journal	December 2013
Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung Balz, Günther; Schiemann, Günther Berichte der deutschen chemischen Gesellschaft (A and B Series), Vol. 60, Issue 5 https://doi.org/10.1002/cber.19270600539	journal	May 1927
Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Aryl Triflates by Deuterium Labeling Milner, Phillip J.; Kinzel, Tom; Zhang, Yong Journal of the American Chemical Society, Vol. 136, Issue 44 https://doi.org/10.1021/ja509144r	journal	October 2014
Dynamic Calcium Metal-Organic Framework Acts as a Selective Organic Solvent Sponge Platero-Prats, Ana E.; de la Peña-O'Shea, Víctor A.; Snejko, Natalia Chemistry - A European Journal, Vol. 16, Issue 38 https://doi.org/10.1002/chem.201001218	journal	August 2010
Metal-organic frameworks as stationary phase for application in chromatographic separation Zhang, Juan; Chen, Zilin Journal of Chromatography A, Vol. 1530 https://doi.org/10.1016/j.chroma.2017.10.065	journal	December 2017
Absolute hardness: companion parameter to absolute electronegativity Parr, Robert G.; Pearson, Ralph G. Journal of the American Chemical Society, Vol. 105, Issue 26 https://doi.org/10.1021/ja00364a005	journal	December 1983
Chromatography in a Single Metal−Organic Framework (MOF) Crystal Han, Shuangbing; Wei, Yanhu; Valente, Cory Journal of the American Chemical Society, Vol. 132, Issue 46 https://doi.org/10.1021/ja1074322	journal	November 2010
How does the Environment Influence a Given Cation? A Systematic Investigation of [Co(CO) ₅ ] ⁺ in Gas Phase, Solution, and Solid State Meier, Stefan C.; Himmel, Daniel; Krossing, Ingo Chemistry – A European Journal, Vol. 24, Issue 72 https://doi.org/10.1002/chem.201804546	journal	November 2018
Monofluorination of Organic Compounds: 10 Years of Innovation Champagne, Pier Alexandre; Desroches, Justine; Hamel, Jean-Denys Chemical Reviews, Vol. 115, Issue 17 https://doi.org/10.1021/cr500706a	journal	April 2015
C−F Bond Activation in Organic Synthesis Amii, Hideki; Uneyama, Kenji Chemical Reviews, Vol. 109, Issue 5 https://doi.org/10.1021/cr800388c	journal	May 2009
Applications of metal-organic frameworks as stationary phases in chromatography Yu, Yuebo; Ren, Yuqian; Shen, Wei TrAC Trends in Analytical Chemistry, Vol. 50 https://doi.org/10.1016/j.trac.2013.04.014	journal	October 2013
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
1,2-Difluorobenzene: a relatively inert and noncoordinating solvent for electrochemical studies on transition-metal complexes O'Toole, Terrence R.; Younathan, Janet N.; Sullivan, B. Patrick Inorganic Chemistry, Vol. 28, Issue 20 https://doi.org/10.1021/ic00319a032	journal	October 1989
Rod Packings and Metal−Organic Frameworks Constructed from Rod-Shaped Secondary Building Units Rosi, Nathaniel L.; Kim, Jaheon; Eddaoudi, Mohamed Journal of the American Chemical Society, Vol. 127, Issue 5, p. 1504-1518 https://doi.org/10.1021/ja045123o	journal	February 2005
Mn ^II -based MIL-53 Analogues: Synthesis Using Neutral Bridging μ ₂ -Ligands and Application in Liquid-Phase Adsorption and Separation of C6−C8 Aromatics Xu, Guohai; Zhang, Xiaoguang; Guo, Peng Journal of the American Chemical Society, Vol. 132, Issue 11 https://doi.org/10.1021/ja910818a	journal	March 2010
¹⁸ F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography Preshlock, Sean; Tredwell, Matthew; Gouverneur, Véronique Chemical Reviews, Vol. 116, Issue 2 https://doi.org/10.1021/acs.chemrev.5b00493	journal	January 2016
Applications of Fluorine in Medicinal Chemistry Gillis, Eric P.; Eastman, Kyle J.; Hill, Matthew D. Journal of Medicinal Chemistry, Vol. 58, Issue 21 https://doi.org/10.1021/acs.jmedchem.5b00258	journal	July 2015
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
Metal–Organic Frameworks for Separations Li, Jian-Rong; Sculley, Julian; Zhou, Hong-Cai Chemical Reviews, Vol. 112, Issue 2, p. 869-932 https://doi.org/10.1021/cr200190s	journal	September 2011
Shape-Selective Sorption and Fluorescence Sensing of Aromatics in a Flexible Network of Tetrakis[(4-methylthiophenyl)ethynyl]silane and AgBF ₄ Huang, Guo; Yang, Chen; Xu, Zhengtao Chemistry of Materials, Vol. 21, Issue 3 https://doi.org/10.1021/cm8027687	journal	February 2009
Complexation and Versatile Reactivity of a Highly Lewis Acidic Cationic Mg Complex with Alkynes and Phosphines Pahl, Jürgen; Stennett, Tom E.; Volland, Michel Chemistry - A European Journal, Vol. 25, Issue 8 https://doi.org/10.1002/chem.201804802	journal	January 2019
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
Three-Dimensional Porous Coordination Polymer Functionalized with Amide Groups Based on Tridentate Ligand: Selective Sorption and Catalysis Hasegawa, Shinpei; Horike, Satoshi; Matsuda, Ryotaro Journal of the American Chemical Society, Vol. 129, Issue 9 https://doi.org/10.1021/ja067374y	journal	March 2007
The reaction of atomic fluorine with fluorobenzene Vasek, Anna Harkins; Sams, Lewis C. Journal of Fluorine Chemistry, Vol. 3, Issue 3-4 https://doi.org/10.1016/S0022-1139(00)82640-8	journal	January 1974
Capture of Carbon Dioxide from Air and Flue Gas in the Alkylamine-Appended Metal–Organic Framework mmen-Mg₂(dobpdc) McDonald, Thomas M.; Lee, Woo Ram; Mason, Jarad A. Journal of the American Chemical Society, Vol. 134, Issue 16, p. 7056-7065 https://doi.org/10.1021/ja300034j	journal	April 2012
Syntheses and Catalytic Hydrogenation Performance of Cationic Bis(phosphine) Cobalt(I) Diene and Arene Compounds Zhong, Hongyu; Friedfeld, Max R.; Chirik, Paul J. Angewandte Chemie International Edition, Vol. 58, Issue 27 https://doi.org/10.1002/anie.201903766	journal	May 2019
Microporous Coordination Polymers As Selective Sorbents for Liquid Chromatography Ahmad, Rashid; Wong-Foy, Antek G.; Matzger, Adam J. Langmuir, Vol. 25, Issue 20 https://doi.org/10.1021/la902276a	journal	October 2009
The Chemistry and Applications of Metal-Organic Frameworks Furukawa, H.; Cordova, K. E.; O'Keeffe, M. Science, Vol. 341, Issue 6149, p. 1230444-1230444 https://doi.org/10.1126/science.1230444	journal	August 2013
Separation of C ₅ -Hydrocarbons on Microporous Materials: Complementary Performance of MOFs and Zeolites Maes, Michael; Alaerts, Luc; Vermoortele, Frederik Journal of the American Chemical Society, Vol. 132, Issue 7 https://doi.org/10.1021/ja9088378	journal	February 2010
From an Easily Accessible Pentacarbonylcobalt(I) Salt to Piano-Stool Cations [(arene)Co(CO) ₂ ] ⁺ Meier, Stefan C.; Holz, Albina; Schmidt, Alexei Chemistry - A European Journal, Vol. 23, Issue 58 https://doi.org/10.1002/chem.201703589	journal	September 2017
Adsorptive separation on metal–organic frameworks in the liquid phase Van de Voorde, Ben; Bueken, Bart; Denayer, Joeri Chem. Soc. Rev., Vol. 43, Issue 16 https://doi.org/10.1039/C4CS00006D	journal	January 2014
Potential of metal–organic frameworks for adsorptive separation of industrially and environmentally relevant liquid mixtures Mukherjee, Soumya; Desai, Aamod V.; Ghosh, Sujit K. Coordination Chemistry Reviews, Vol. 367 https://doi.org/10.1016/j.ccr.2018.04.001	journal	July 2018
Separation of Xylene Isomers through Multiple Metal Site Interactions in Metal–Organic Frameworks Gonzalez, Miguel I.; Kapelewski, Matthew T.; Bloch, Eric D. Journal of the American Chemical Society, Vol. 140, Issue 9 https://doi.org/10.1021/jacs.7b13825	journal	February 2018
Metal-Organic Frameworks from Edible Natural Products Smaldone, Ronald A.; Forgan, Ross S.; Furukawa, Hiroyasu Angewandte Chemie International Edition, Vol. 49, Issue 46, p. 8630-8634 https://doi.org/10.1002/anie.201002343	journal	August 2010
Access to the Bis-benzene Cobalt(I) Sandwich Cation and its Derivatives: Synthons for a “Naked” Cobalt(I) Source? Meier, Stefan C.; Holz, Albina; Kulenkampff, Jan Angewandte Chemie International Edition, Vol. 57, Issue 30 https://doi.org/10.1002/anie.201803108	journal	June 2018
Search for improved fluorinated stationary phases for separation of fluorine-containing pharmaceuticals from their desfluoro analogs Regalado, Erik L.; Makarov, Alexey A.; McClain, Ray Journal of Chromatography A, Vol. 1380 https://doi.org/10.1016/j.chroma.2014.12.025	journal	February 2015
A Fluorobenzene Adduct of Ti(IV), and Catalytic Carboamination to Prepare α,β-Unsaturated Imines and Triaryl-Substituted Quinolines Basuli, Falguni; Aneetha, Halikhedkar; Huffman, John C. Journal of the American Chemical Society, Vol. 127, Issue 51 https://doi.org/10.1021/ja0566026	journal	December 2005
Large-Pore Apertures in a Series of Metal-Organic Frameworks Deng, H.; Grunder, S.; Cordova, K. E. Science, Vol. 336, Issue 6084, p. 1018-1023 https://doi.org/10.1126/science.1220131	journal	May 2012

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Title: Fluoroarene Separations in Metal-Organic Frameworks with Two Proximal Mg2+ Coordination Sites

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