Interpenetration Isomerism in Triptycene‐Based Hydrogen‐Bonded Organic Frameworks

Li, Penghao; Li, Peng; Ryder, Matthew R.; Liu, Zhichang; Stern, Charlotte L.; Farha, Omar K.; Stoddart, J. Fraser

doi:10.1002/ange.201811263

Title: Interpenetration Isomerism in Triptycene‐Based Hydrogen‐Bonded Organic Frameworks

Journal Article · Wed Jan 09 00:00:00 EST 2019 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201811263· OSTI ID:1579761

^[1];

^[2];

^[3];

^[1];

^[4]

Department of Chemistry Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
Neutron Scattering Division Oak Ridge National Laboratory Oak Ridge TN 37831 USA
School of Science Westlake University 18 Shilongshan Road Hangzhou 310024 China
Department of Chemistry Northwestern University 2145 Sheridan Road Evanston IL 60208 USA, Institute for Molecular Design and Synthesis Tianjin University 92 Weijin Road Tianjin 300072 China, School of Chemistry University of New South Wales Sydney NSW 2052 Australia

Abstract We describe an example of “interpenetration isomerism” in three‐dimensional hydrogen‐bonded organic frameworks. By exploiting the crystallization conditions for a peripherally extended triptycene H ₆ PET, we can modulate the interpenetration of the assembled frameworks, yielding a two‐fold interpenetrated structure PETHOF‐ 1 and a five‐fold interpenetrated structure PETHOF‐ 2 as interpenetration isomers. In PETHOF‐ 1 , two individual nets are related by inversion symmetry and form an interwoven topology with a large guest‐accessible volume of about 80 %. In PETHOF‐ 2 , five individual nets are related by translational symmetry and are stacked in an alternating fashion. The activated materials show permanent porosity with Brunauer‐Emmett‐Teller surface areas exceeding 1100 m ² g ⁻¹ . Synthetic control over the framework interpenetration could serve as a new strategy to construct complex supramolecular architectures from simple organic building blocks.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

OSTI ID:: 1579761

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 131 Journal Issue: 6; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (70)

Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis Desiraju, Gautam R. Angewandte Chemie International Edition in English, Vol. 34, Issue 21 https://doi.org/10.1002/anie.199523111	journal	November 1995
Dissecting Porosity in Molecular Crystals: Influence of Geometry, Hydrogen Bonding, and [π···π] Stacking on the Solid-State Packing of Fluorinated Aromatics Hashim, Mohamed I.; Le, Ha T. M.; Chen, Teng-Hao Journal of the American Chemical Society, Vol. 140, Issue 18 https://doi.org/10.1021/jacs.8b02869	journal	April 2018
Deconstruction of Crystalline Networks into Underlying Nets: Relevance for Terminology Guidelines and Crystallographic Databases Bonneau, Charlotte; O’Keeffe, Michael; Proserpio, Davide M. Crystal Growth & Design, Vol. 18, Issue 6 https://doi.org/10.1021/acs.cgd.8b00126	journal	May 2018
A Rod-Packing Microporous Hydrogen-Bonded Organic Framework for Highly Selective Separation of C ₂ H ₂ /CO ₂ at Room Temperature Li, Peng; He, Yabing; Zhao, Yunfeng Angewandte Chemie International Edition https://doi.org/10.1002/anie.201410077	journal	November 2014
Isomerism in Metal–Organic Frameworks: “Framework Isomers” Makal, Trevor A.; Yakovenko, Andrey A.; Zhou, Hong-Cai The Journal of Physical Chemistry Letters, Vol. 2, Issue 14 https://doi.org/10.1021/jz200424h	journal	June 2011
A Series of Layered Assemblies of Hydrogen-Bonded, Hexagonal Networks of C ₃ -Symmetric π-Conjugated Molecules: A Potential Motif of Porous Organic Materials Hisaki, Ichiro; Nakagawa, Shoichi; Ikenaka, Nobuaki Journal of the American Chemical Society, Vol. 138, Issue 20 https://doi.org/10.1021/jacs.6b02968	journal	May 2016
A Robust Binary Supramolecular Organic Framework (SOF) with High CO ₂ Adsorption and Selectivity Lü, Jian; Perez-Krap, Cristina; Suyetin, Mikhail Journal of the American Chemical Society, Vol. 136, Issue 37 https://doi.org/10.1021/ja506577g	journal	September 2014
Molecular Tectonics. Selective Exchange of Cations in Porous Anionic Hydrogen-Bonded Networks Built from Derivatives of Tetraphenylborate Malek, Nadia; Maris, Thierry; Simard, Michel Journal of the American Chemical Society, Vol. 127, Issue 16 https://doi.org/10.1021/ja042233m	journal	April 2005
Two solvent-induced porous hydrogen-bonded organic frameworks: solvent effects on structures and functionalities Wang, Hailong; Bao, Zongbi; Wu, Hui Chemical Communications, Vol. 53, Issue 81 https://doi.org/10.1039/C7CC06187K	journal	January 2017
Computational structure characterisation tools in application to ordered and disordered porous materials Sarkisov, Lev; Harrison, Alex Molecular Simulation, Vol. 37, Issue 15 https://doi.org/10.1080/08927022.2011.592832	journal	December 2011
Engineering Hydrogen-Bonded Molecular Crystals Built from Derivatives of Hexaphenylbenzene and Related Compounds Maly, Kenneth E.; Gagnon, Eric; Maris, Thierry Journal of the American Chemical Society, Vol. 129, Issue 14 https://doi.org/10.1021/ja067571x	journal	April 2007
Docking Strategy To Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area Hisaki, Ichiro; Suzuki, Yuto; Gomez, Eduardo Angewandte Chemie International Edition, Vol. 57, Issue 39 https://doi.org/10.1002/anie.201805472	journal	July 2018
Catenated and non-catenated inclusion complexes of trimesic acid Herbstein, F. H.; Kapon, M.; Reisner, G. M. Journal of Inclusion Phenomena, Vol. 5, Issue 2 https://doi.org/10.1007/BF00655650	journal	April 1987
A Solid-State Chemist's View of the Crystal Polymorphism of Organic Compounds Gavezzotti, Angelo Journal of Pharmaceutical Sciences, Vol. 96, Issue 9 https://doi.org/10.1002/jps.20870	journal	September 2007
A C ₃ -Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals Hisaki, Ichiro; Nakagawa, Shoichi; Tohnai, Norimitsu Angewandte Chemie International Edition, Vol. 54, Issue 10 https://doi.org/10.1002/anie.201411438	journal	January 2015
A permanently porous single molecule H-bonded organic framework for selective CO ₂ capture Nandi, Shyamapada; Chakraborty, Debanjan; Vaidhyanathan, Ramanathan Chemical Communications, Vol. 52, Issue 45 https://doi.org/10.1039/C6CC02964G	journal	January 2016
Novel triptycene-derived hosts: synthesis and their applications in supramolecular chemistry Chen, Chuan-Feng Chemical Communications, Vol. 47, Issue 6 https://doi.org/10.1039/c0cc04852f	journal	January 2011
Activation of metal–organic framework materials Mondloch, Joseph E.; Karagiaridi, Olga; Farha, Omar K. CrystEngComm, Vol. 15, Issue 45 https://doi.org/10.1039/c3ce41232f	journal	January 2013
Molecular Tectonics. Porous Hydrogen-Bonded Networks Built from Derivatives of 9,9‘-Spirobifluorene Fournier, Jean-Hugues; Maris, Thierry; Wuest, James D. The Journal of Organic Chemistry, Vol. 69, Issue 6 https://doi.org/10.1021/jo0348118	journal	March 2004
Engineering crystals by the strategy of molecular tectonics Wuest, James D. Chemical Communications, Issue 47 https://doi.org/10.1039/b512641j	journal	January 2005
Understanding and Controlling the Dielectric Response of Metal-Organic Frameworks Ryder, Matthew R.; Donà, Lorenzo; Vitillo, Jenny G. ChemPlusChem, Vol. 83, Issue 4 https://doi.org/10.1002/cplu.201700558	journal	March 2018
An Ultra-Robust and Crystalline Redeemable Hydrogen-Bonded Organic Framework for Synergistic Chemo-Photodynamic Therapy Yin, Qi; Zhao, Peng; Sa, Rong-Jian Angewandte Chemie, Vol. 130, Issue 26 https://doi.org/10.1002/ange.201800354	journal	June 2018
Introduction to Metal–Organic Frameworks Zhou, Hong-Cai; Long, Jeffrey R.; Yaghi, Omar M. Chemical Reviews, Vol. 112, Issue 2, p. 673-674 https://doi.org/10.1021/cr300014x	journal	September 2011
An Ultrastable and Easily Regenerated Hydrogen-Bonded Organic Molecular Framework with Permanent Porosity Hu, Falu; Liu, Caiping; Wu, Mingyan Angewandte Chemie, Vol. 129, Issue 8 https://doi.org/10.1002/ange.201610901	journal	January 2017
Observation of Interpenetration Isomerism in Covalent Organic Frameworks Ma, Tianqiong; Li, Jian; Niu, Jing Journal of the American Chemical Society, Vol. 140, Issue 22 https://doi.org/10.1021/jacs.8b03169	journal	April 2018
Exceptional Thermal Stability in a Supramolecular Organic Framework: Porosity and Gas Storage Yang, Wenbin; Greenaway, Alex; Lin, Xiang Journal of the American Chemical Society, Vol. 132, Issue 41 https://doi.org/10.1021/ja1042935	journal	October 2010
Interpenetrating metal-organic and inorganic 3D networks: a computer-aided systematic investigation. Part II [1]. Analysis of the Inorganic Crystal Structure Database (ICSD) Baburin, I. A.; Blatov, V. A.; Carlucci, L. Journal of Solid State Chemistry, Vol. 178, Issue 8 https://doi.org/10.1016/j.jssc.2005.05.029	journal	August 2005
Docking Strategy To Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area Hisaki, Ichiro; Suzuki, Yuto; Gomez, Eduardo Angewandte Chemie, Vol. 130, Issue 39 https://doi.org/10.1002/ange.201805472	journal	July 2018
BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions van der Sluis, P.; Spek, A. L. Acta Crystallographica Section A Foundations of Crystallography, Vol. 46, Issue 3 https://doi.org/10.1107/S0108767389011189	journal	March 1990
Thermally robust and porous noncovalent organic framework with high affinity for fluorocarbons and CFCs Chen, Teng-Hao; Popov, Ilya; Kaveevivitchai, Watchareeya Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6131	journal	October 2014
Crystal Engineering: From Molecule to Crystal Desiraju, Gautam R. Journal of the American Chemical Society, Vol. 135, Issue 27 https://doi.org/10.1021/ja403264c	journal	June 2013
Function-led design of new porous materials Slater, A. G.; Cooper, A. I. Science, Vol. 348, Issue 6238 https://doi.org/10.1126/science.aaa8075	journal	May 2015
An Ultrastable and Easily Regenerated Hydrogen-Bonded Organic Molecular Framework with Permanent Porosity Hu, Falu; Liu, Caiping; Wu, Mingyan Angewandte Chemie International Edition, Vol. 56, Issue 8 https://doi.org/10.1002/anie.201610901	journal	January 2017
The atom, the molecule, and the covalent organic framework Diercks, Christian S.; Yaghi, Omar M. Science, Vol. 355, Issue 6328 https://doi.org/10.1126/science.aal1585	journal	March 2017
Preparation of Tri- and Hexasubstituted Triptycene Synthons by Transition Metal Catalyzed Cross-Coupling Reactions for Post-Modifications: Preparation of Tri- and Hexasubstituted Triptycene Synthons Moylan, Claire; Rogers, Luke; Shaker, Yasser M. European Journal of Organic Chemistry, Vol. 2016, Issue 1 https://doi.org/10.1002/ejoc.201501272	journal	December 2015
A Homochiral Microporous Hydrogen-Bonded Organic Framework for Highly Enantioselective Separation of Secondary Alcohols Li, Peng; He, Yabing; Guang, Jie Journal of the American Chemical Society, Vol. 136, Issue 2 https://doi.org/10.1021/ja4129795	journal	January 2014
A Molecular Propeller with Three Nanohoop Blades: Synthesis, Characterization, and Solid-State Packing Li, Penghao; Zakharov, Lev N.; Jasti, Ramesh Angewandte Chemie, Vol. 129, Issue 19 https://doi.org/10.1002/ange.201700935	journal	April 2017
Covalent organic frameworks: a materials platform for structural and functional designs Huang, Ning; Wang, Ping; Jiang, Donglin Nature Reviews Materials, Vol. 1, Issue 10 https://doi.org/10.1038/natrevmats.2016.68	journal	September 2016
Selective CO ₂ Adsorption in a Supramolecular Organic Framework Patil, Rahul S.; Banerjee, Debasis; Zhang, Chen Angewandte Chemie International Edition, Vol. 55, Issue 14 https://doi.org/10.1002/anie.201600658	journal	March 2016
The role of reticular chemistry in the design of CO2 reduction catalysts Diercks, Christian S.; Liu, Yuzhong; Cordova, Kyle E. Nature Materials, Vol. 17, Issue 4 https://doi.org/10.1038/s41563-018-0033-5	journal	February 2018
From Molecules to Crystal Engineering: Supramolecular Isomerism and Polymorphism in Network Solids Moulton, Brian; Zaworotko, Michael J. Chemical Reviews, Vol. 101, Issue 6 https://doi.org/10.1021/cr9900432	journal	June 2001
How Interpenetration Ensures Rigidity and Permanent Porosity in a Highly Flexible Hybrid Solid Dan-Hardi, Meenakshi; Chevreau, Hubert; Devic, Thomas Chemistry of Materials, Vol. 24, Issue 13 https://doi.org/10.1021/cm300450x	journal	June 2012
A Hydrogen-Bonded Hexagonal Buckybowl Framework Hisaki, Ichiro; Toda, Hideaki; Sato, Hiroyasu Angewandte Chemie International Edition, Vol. 56, Issue 48 https://doi.org/10.1002/anie.201708115	journal	October 2017
Applied Topological Analysis of Crystal Structures with the Program Package ToposPro Blatov, Vladislav A.; Shevchenko, Alexander P.; Proserpio, Davide M. Crystal Growth & Design, Vol. 14, Issue 7 https://doi.org/10.1021/cg500498k	journal	May 2014
Interpenetration control in metal–organic frameworks for functional applications Jiang, Hai-Long; Makal, Trevor A.; Zhou, Hong-Cai Coordination Chemistry Reviews, Vol. 257, Issue 15-16 https://doi.org/10.1016/j.ccr.2013.03.017	journal	August 2013
Negative Thermal Expansion in the Metal-Organic Framework Material Cu ₃ (1,3,5-benzenetricarboxylate) ₂ Wu, Yue; Kobayashi, Atsushi; Halder, Gregory J. Angewandte Chemie International Edition, Vol. 47, Issue 46 https://doi.org/10.1002/anie.200803925	journal	November 2008
Rational Construction of an Extrinsic Porous Molecular Crystal with an Extraordinary High Specific Surface Area Mastalerz, Michael; Oppel, Iris M. Angewandte Chemie International Edition, Vol. 51, Issue 21 https://doi.org/10.1002/anie.201201174	journal	March 2012
A Flexible Microporous Hydrogen-Bonded Organic Framework for Gas Sorption and Separation Wang, Hailong; Li, Bin; Wu, Hui Journal of the American Chemical Society, Vol. 137, Issue 31 https://doi.org/10.1021/jacs.5b05644	journal	July 2015
Double−Step Gas Sorption of a Two−Dimensional Metal−Organic Framework Kondo, Atsushi; Noguchi, Hiroshi; Carlucci, Lucia Journal of the American Chemical Society, Vol. 129, Issue 41 https://doi.org/10.1021/ja073568h	journal	October 2007
Interpenetrated Three-Dimensional Networks of Hydrogen-Bonded Organic Species: A Systematic Analysis of the Cambridge Structural Database Baburin, Igor A.; Blatov, Vladislav A.; Carlucci, Lucia Crystal Growth & Design, Vol. 8, Issue 2 https://doi.org/10.1021/cg0705660	journal	February 2008
Porous Organic Molecular Frameworks with Extrinsic Porosity: A Platform for Carbon Storage and Separation Lü, Jian; Cao, Rong Angewandte Chemie International Edition, Vol. 55, Issue 33 https://doi.org/10.1002/anie.201602116	journal	July 2016
A Rod-Packing Microporous Hydrogen-Bonded Organic Framework for Highly Selective Separation of C ₂ H ₂ /CO ₂ at Room Temperature Li, Peng; He, Yabing; Zhao, Yunfeng Angewandte Chemie, Vol. 127, Issue 2 https://doi.org/10.1002/ange.201410077	journal	November 2014
Single-crystal structure validation with the program PLATON Spek, A. L. Journal of Applied Crystallography, Vol. 36, Issue 1, p. 7-13 https://doi.org/10.1107/S0021889802022112	journal	January 2003
Interpenetrating metal–organic and inorganic 3D networks: a computer-aided systematic investigation. Part I. Analysis of the Cambridge structural database Blatov, V. A.; Carlucci, L.; Ciani, G. CrystEngComm, Vol. 6, Issue 65 https://doi.org/10.1039/B409722J	journal	January 2004
A Molecular Propeller with Three Nanohoop Blades: Synthesis, Characterization, and Solid-State Packing Li, Penghao; Zakharov, Lev N.; Jasti, Ramesh Angewandte Chemie International Edition, Vol. 56, Issue 19 https://doi.org/10.1002/anie.201700935	journal	April 2017
Supercritical Processing as a Route to High Internal Surface Areas and Permanent Microporosity in Metal−Organic Framework Materials Nelson, Andrew P.; Farha, Omar K.; Mulfort, Karen L. Journal of the American Chemical Society, Vol. 131, Issue 2, p. 458-460 https://doi.org/10.1021/ja808853q	journal	January 2009
Very Large Breathing Effect in the First Nanoporous Chromium(III)-Based Solids MIL-53 or Cr^III(OH)·{O₂C−C₆H₄−CO₂}·{HO₂C−C₆H₄−CO₂H}_x·H₂O_y Serre, Christian; Millange, Franck; Thouvenot, Christelle Journal of the American Chemical Society, Vol. 124, Issue 45, p. 13519-13526 https://doi.org/10.1021/ja0276974	journal	November 2002
A Microporous Hydrogen-Bonded Organic Framework for Highly Selective C ₂ H ₂ /C ₂ H ₄ Separation at Ambient Temperature He, Yabing; Xiang, Shengchang; Chen, Banglin Journal of the American Chemical Society, Vol. 133, Issue 37 https://doi.org/10.1021/ja2066016	journal	September 2011
Grand Challenges and Future Opportunities for Metal–Organic Frameworks Hendon, Christopher H.; Rieth, Adam J.; Korzyński, Maciej D. ACS Central Science, Vol. 3, Issue 6 https://doi.org/10.1021/acscentsci.7b00197	journal	June 2017
Supramolekulare Synthone für das Kristall-Engineering - eine neue organische Synthese Desiraju, Gautam R. Angewandte Chemie, Vol. 107, Issue 21 https://doi.org/10.1002/ange.19951072105	journal	November 1995
Selective CO ₂ Adsorption in a Supramolecular Organic Framework Patil, Rahul S.; Banerjee, Debasis; Zhang, Chen Angewandte Chemie, Vol. 128, Issue 14 https://doi.org/10.1002/ange.201600658	journal	March 2016
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
A Hydrogen-Bonded Hexagonal Buckybowl Framework Hisaki, Ichiro; Toda, Hideaki; Sato, Hiroyasu Angewandte Chemie, Vol. 129, Issue 48 https://doi.org/10.1002/ange.201708115	journal	October 2017
Organische molekulare Gerüste mit extrinsischer Porosität: eine Plattform für die Kohlendioxid-Abscheidung und Speicherung Lü, Jian; Cao, Rong Angewandte Chemie, Vol. 128, Issue 33 https://doi.org/10.1002/ange.201602116	journal	July 2016
An Ultra-Robust and Crystalline Redeemable Hydrogen-Bonded Organic Framework for Synergistic Chemo-Photodynamic Therapy Yin, Qi; Zhao, Peng; Sa, Rong-Jian Angewandte Chemie International Edition, Vol. 57, Issue 26 https://doi.org/10.1002/anie.201800354	journal	June 2018
Negative Thermal Expansion in the Metal-Organic Framework Material Cu ₃ (1,3,5-benzenetricarboxylate) ₂ Wu, Yue; Kobayashi, Atsushi; Halder, Gregory J. Angewandte Chemie, Vol. 120, Issue 46 https://doi.org/10.1002/ange.200803925	journal	November 2008
Rationale Herstellung eines extrinsisch porösen Molekülkristalls mit einer außergewöhnlich großen spezifischen Oberfläche Mastalerz, Michael; Oppel, Iris M. Angewandte Chemie, Vol. 124, Issue 21 https://doi.org/10.1002/ange.201201174	journal	March 2012
A C ₃ -Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals Hisaki, Ichiro; Nakagawa, Shoichi; Tohnai, Norimitsu Angewandte Chemie, Vol. 127, Issue 10 https://doi.org/10.1002/ange.201411438	journal	February 2015
Metal–Organic Frameworks as Platforms for Functional Materials Cui, Yuanjing; Li, Bin; He, Huajun Accounts of Chemical Research, Vol. 49, Issue 3 https://doi.org/10.1021/acs.accounts.5b00530	journal	February 2016
Predictably Ordered Open Hydrogen-Bonded Networks Built from Indeno[1,2- b ]fluorenes Beaudoin, Daniel; Blair-Pereira, Joao-Nicolas; Langis-Barsetti, Sophie The Journal of Organic Chemistry, Vol. 82, Issue 16 https://doi.org/10.1021/acs.joc.7b01333	journal	July 2017

Similar Records

“Interpenetration Isomerism” of Triptycene-Based Hydrogen-Bonded Organic Frameworks

Journal Article · Tue Dec 11 00:00:00 EST 2018 · Angewandte Chemie (International Edition) · OSTI ID:1579761

Li, Penghao; Li, Peng; Ryder, Matthew R.; +4 more

Organic Counteranion Co-assembly Strategy for the Formation of γ-Cyclodextrin-Containing Hybrid Frameworks

Journal Article · Tue Jan 14 00:00:00 EST 2020 · Journal of the American Chemical Society · OSTI ID:1579761

Shen, Dengke; Cooper, James A.; Li, Peng; +15 more

Partially Interpenetrated NbO Topology Metal–Organic Framework Exhibiting Selective Gas Adsorption

Journal Article · Wed Mar 29 00:00:00 EDT 2017 · Crystal Growth and Design · OSTI ID:1579761

Verma, Gaurav; Kumar, Sanjay; Pham, Tony; +5 more

Title: Interpenetration Isomerism in Triptycene‐Based Hydrogen‐Bonded Organic Frameworks

Citation Formats

References (70)

Similar Records

Related Subjects