Supramolecular binding and separation of hydrocarbons within a functionalized porous metal–organic framework

Yang, Sihai; Ramirez-Cuesta, Anibal J.; Newby, Ruth; Garcia-Sakai, Victoria; Manuel, Pascal; Callear, Samantha K.; Campbell, Stuart I.; Tang, Chiu C.; Schröder, Martin

doi:10.1038/nchem.2114

Title: Supramolecular binding and separation of hydrocarbons within a functionalized porous metal–organic framework

Journal Article · Mon Dec 01 00:00:00 EST 2014 · Nature Chemistry

DOI:https://doi.org/10.1038/nchem.2114· OSTI ID:1286811

Yang, Sihai; Ramirez-Cuesta, Anibal J.; Newby, Ruth; Garcia-Sakai, Victoria; Manuel, Pascal; Callear, Samantha K.; Campbell, Stuart I.; Tang, Chiu C.; Schröder, Martin

Supramolecular interactions are fundamental to host-guest binding in many chemical and biological processes. Direct visualization of such supramolecular interactions within host-guest systems is extremely challenging, but crucial to understanding their function. We report a comprehensive study that combines neutron scattering, synchrotron X-ray and neutron diffraction, and computational modelling to define the detailed binding at a molecular level of acetylene, ethylene and ethane within the porous host NOTT-300. This study reveals simultaneous and cooperative hydrogen-bonding, pi center dot center dot center dot pi stacking interactions and intermolecular dipole interactions in the binding of acetylene and ethylene to give up to 12 individual weak supramolecular interactions aligned within the host to form an optimal geometry for the selective binding of hydrocarbons. We also report the cooperative binding of a mixture of acetylene and ethylene within the porous host, together with the corresponding breakthrough experiments and analysis of adsorption isotherms of gas mixtures.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Oak Ridge Leadership Computing Facility (OLCF)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1286811

Alternate ID(s):: OSTI ID: 1352748

Journal Information:: Nature Chemistry, Vol. 7, Issue 2; ISSN 1755-4330

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 433 works

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Metal-Organic Frameworks for Separation Zhao, Xiang; Wang, Yanxiang; Li, Dong-Sheng Advanced Materials, Vol. 30, Issue 37 https://doi.org/10.1002/adma.201705189	journal	March 2018
A Single-Molecule Propyne Trap: Highly Efficient Removal of Propyne from Propylene with Anion-Pillared Ultramicroporous Materials Yang, Lifeng; Cui, Xili; Yang, Qiwei Advanced Materials, Vol. 30, Issue 10 https://doi.org/10.1002/adma.201705374	journal	January 2018
A Chemically Stable Hofmann‐Type Metal−Organic Framework with Sandwich‐Like Binding Sites for Benchmark Acetylene Capture Pei, Jiyan; Shao, Kai; Wang, Jia‐Xin Advanced Materials https://doi.org/10.1002/adma.201908275	journal	May 2020
Simultaneous Trapping of C ₂ H ₂ and C ₂ H ₆ from a Ternary Mixture of C ₂ H ₂ /C ₂ H ₄ /C ₂ H ₆ in a Robust Metal–Organic Framework for the Purification of C ₂ H ₄ Hao, Hong‐Guo; Zhao, Yun‐Feng; Chen, Di‐Ming Angewandte Chemie, Vol. 130, Issue 49 https://doi.org/10.1002/ange.201809884	journal	October 2018
Selective Aerobic Oxidation of a Metal–Organic Framework Boosts Thermodynamic and Kinetic Propylene/Propane Selectivity Wang, Yu; Huang, Ning‐Yu; Zhang, Xue‐Wen Angewandte Chemie, Vol. 131, Issue 23 https://doi.org/10.1002/ange.201902209	journal	May 2019
Robust Microporous Metal–Organic Frameworks for Highly Efficient and Simultaneous Removal of Propyne and Propadiene from Propylene Peng, Yun‐Lei; He, Chaohui; Pham, Tony Angewandte Chemie, Vol. 131, Issue 30 https://doi.org/10.1002/ange.201904312	journal	June 2019
Molecular Sieving of Ethane from Ethylene through the Molecular Cross-Section Size Differentiation in Gallate-based Metal-Organic Frameworks Bao, Zongbi; Wang, Jiawei; Zhang, Zhiguo Angewandte Chemie International Edition, Vol. 57, Issue 49 https://doi.org/10.1002/anie.201808716	journal	November 2018
Simultaneous Trapping of C ₂ H ₂ and C ₂ H ₆ from a Ternary Mixture of C ₂ H ₂ /C ₂ H ₄ /C ₂ H ₆ in a Robust Metal-Organic Framework for the Purification of C ₂ H ₄ Hao, Hong-Guo; Zhao, Yun-Feng; Chen, Di-Ming Angewandte Chemie International Edition, Vol. 57, Issue 49 https://doi.org/10.1002/anie.201809884	journal	November 2018
Extraordinary Separation of Acetylene-Containing Mixtures with Microporous Metal-Organic Frameworks with Open O Donor Sites and Tunable Robustness through Control of the Helical Chain Secondary Building Units Yao, Zizhu; Zhang, Zhangjing; Liu, Lizhen Chemistry - A European Journal, Vol. 22, Issue 16 https://doi.org/10.1002/chem.201505107	journal	March 2016
Charge Control in Two Isostructural Anionic/Cationic Co ^II Coordination Frameworks for Enhanced Acetylene Capture Chen, Di-Ming; Tian, Jia-Yue; Liu, Chun-Sen Chemistry - A European Journal, Vol. 22, Issue 42 https://doi.org/10.1002/chem.201603054	journal	September 2016
An ultra-tunable platform for molecular engineering of high-performance crystalline porous materials Zhai, Quan-Guo; Bu, Xianhui; Mao, Chengyu Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13645	journal	December 2016
Unravelling exceptional acetylene and carbon dioxide adsorption within a tetra-amide functionalized metal-organic framework Moreau, Florian; da Silva, Ivan; Al Smail, Nada H. Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms14085	journal	February 2017
A stable zirconium based metal-organic framework for specific recognition of representative polychlorinated dibenzo-p-dioxin molecules Wang, Bin; Wang, Peilong; Xie, Lin-Hua Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-11912-4	journal	August 2019
Structural, energetic and dynamic insights into the abnormal xylene separation behavior of hierarchical porous crystal Lin, Jiao-Min; He, Chun-Ting; Liao, Pei-Qin Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep11537	journal	June 2015
Metallopolymers for advanced sustainable applications Wang, Yanlan; Astruc, Didier; Abd-El-Aziz, Alaa S. Chemical Society Reviews, Vol. 48, Issue 2 https://doi.org/10.1039/c7cs00656j	journal	January 2019
Chiral metal–organic frameworks constructed from four-fold helical chain SBUs for enantioselective recognition of α-hydroxy/amino acids Yao, Ru-Xin; Fu, Huan-Huan; Yu, Bo Inorganic Chemistry Frontiers, Vol. 5, Issue 1 https://doi.org/10.1039/c7qi00615b	journal	January 2018
Metal–organic frameworks in seconds via selective microwave heating Laybourn, Andrea; Katrib, Juliano; Ferrari-John, Rebecca S. Journal of Materials Chemistry A, Vol. 5, Issue 16 https://doi.org/10.1039/c7ta01493g	journal	January 2017
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Separation of Acetylene from Carbon Dioxide and Ethylene by a Water-Stable Microporous Metal-Organic Framework with Aligned Imidazolium Groups inside the Channels Lee, Jaechul; Chuah, Chong Yang; Kim, Jaheon Angewandte Chemie, Vol. 130, Issue 26 https://doi.org/10.1002/ange.201804442	journal	May 2018
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Robust Microporous Metal-Organic Frameworks for Highly Efficient and Simultaneous Removal of Propyne and Propadiene from Propylene Peng, Yun-Lei; He, Chaohui; Pham, Tony Angewandte Chemie International Edition, Vol. 58, Issue 30 https://doi.org/10.1002/anie.201904312	journal	June 2019
An Allosteric Metal–Organic Framework That Exhibits Multiple Pore Configurations for the Optimization of Hydrocarbon Separation Zhou, Beibei; Zeng, Tengwu; Shi, Zhao‐Lin Chemistry – An Asian Journal, Vol. 14, Issue 20 https://doi.org/10.1002/asia.201900239	journal	May 2019
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Titelbild: Separation of Xe from Kr with Record Selectivity and Productivity in Anion‐Pillared Ultramicroporous Materials by Inverse Size‐Sieving (Angew. Chem. 9/2020) Wang, Qingju; Ke, Tian; Yang, Lifeng Angewandte Chemie, Vol. 132, Issue 9 https://doi.org/10.1002/ange.202000349	journal	January 2020
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Molecular Sieving of Ethane from Ethylene through the Molecular Cross‐Section Size Differentiation in Gallate‐based Metal–Organic Frameworks Bao, Zongbi; Wang, Jiawei; Zhang, Zhiguo Angewandte Chemie, Vol. 130, Issue 49 https://doi.org/10.1002/ange.201808716	journal	October 2018
Ammonia Storage by Reversible Host-Guest Site Exchange in a Robust Metal-Organic Framework Godfrey, Harry G. W.; da Silva, Ivan; Briggs, Lydia Angewandte Chemie International Edition, Vol. 57, Issue 45 https://doi.org/10.1002/anie.201808316	journal	October 2018
Cover Picture: Separation of Xe from Kr with Record Selectivity and Productivity in Anion‐Pillared Ultramicroporous Materials by Inverse Size‐Sieving (Angew. Chem. Int. Ed. 9/2020) Wang, Qingju; Ke, Tian; Yang, Lifeng Angewandte Chemie International Edition, Vol. 59, Issue 9 https://doi.org/10.1002/anie.202000349	journal	January 2020
Fine-Tuning the Pore Environment of the Microporous Cu-MOF for High Propylene Storage and Efficient Separation of Light Hydrocarbons Fan, Weidong; Wang, Xia; Zhang, Xiurong ACS Central Science, Vol. 5, Issue 7 https://doi.org/10.1021/acscentsci.9b00423	journal	June 2019

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Metal–organic frameworks

CCDC 1028617: Experimental Crystal Structure Determination: TOXMUQ : catena-[(μ-biphenyl-3,3',5,5'-tetracarboxylato)-bis(μ-hydroxo)-di-aluminium tetrakis(acetylene)] Yang, Sihai; Ramirez-Cuesta, Anibal J.; Newby, Ruth https://doi.org/10.5517/cc13jc66 The current record is supplemented by this dataset	dataset	October 2014
CCDC 1028618: Experimental Crystal Structure Determination: TOXNAX : catena-[bis((μ-biphenyl-3,3',5,5'-tetracarboxylato)-bis(μ-hydroxo)-di-aluminium) pentakis(ethylene)] Yang, Sihai; Ramirez-Cuesta, Anibal; Newby, Ruth https://doi.org/10.5517/cc13jc77 The current record is supplemented by this dataset	dataset	October 2014
CCDC 1028620: Experimental Crystal Structure Determination: TOXNIF : catena-[bis((μ-biphenyl-3,3',5,5'-tetracarboxylato)-bis(μ-hydroxo)-di-aluminium) perdeuteroethylene] Space Group: I 41 2 2 (98), Cell: a 14.794232(96)Å b 14.794232(96)Å c 11.77851(18)Å, α 90° β 90° γ 90° Yang, Sihai; Ramirez-Cuesta, Anibal J.; Newby, Ruth https://doi.org/10.5517/cc13jc99 The current record is supplemented by this dataset	dataset	October 2014
CCDC 1028619: Experimental Crystal Structure Determination: TOXNEB : catena-[(μ-biphenyl-3,3',5,5'-tetracarboxylato)-bis(μ-hydroxo)-di-aluminium perdeuteroacetylene] Yang, Sihai; Ramirez-Cuesta, Anibal; Newby, Ruth https://doi.org/10.5517/cc13jc88 The current record is supplemented by this dataset	dataset	October 2014
CCDC 1028621: Experimental Crystal Structure Determination: XUPSAE : catena-[(μ8-Biphenyl-3,3',5,5'-tetracarboxylato)-bis(μ2-hydroxo)-di-aluminium deuteroethane solvate] Yang, Sihai; Ramirez-Cuesta, Anibal; Newby, Ruth https://doi.org/10.5517/cc13jcbb The current record is supplemented by this dataset	dataset	October 2014