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

Abstract

In this work, we describe an example of “interpenetration isomerism” in three-dimensional (3D) hydrogen-bonded organic frameworks (HOFs). By exploiting the crystallization conditions for a peripherally extended triptycene H6PET, we can modulate the interpenetration of the assembled frameworks, yielding a two-fold interpenetrated structure PETHOF-1 (acs-2c topology) and a five-fold interpenetrated structure PETHOF-2 (acs-5c topology) as “interpenetration isomers”. In PETHOF-1, two individual nets are related by inversion symmetry and form an interwoven topology with a strikingly 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. Additionally, the activated materials show permanent porosity with high Brunauer–Emmett–Teller (BET) areas exceeding 1100 m2•g-1. Finally, we believe that synthetic control over the framework interpenetration can serve as a new design strategy to construct diverse and complex supramolecular architectures from simple organic building blocks.

Authors:
 [1];  [1];  [2];  [3];  [1];  [1];  [4]
  1. Northwestern Univ., Evanston, IL (United States)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  3. Westlake University, Hangzhou (China)
  4. Northwestern Univ., Evanston, IL (United States); Tianjin University (China); University of New South Wales, Sydney (Australia)
Publication Date:
Research Org.:
Univ. of Notre Dame, IN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities Division
OSTI Identifier:
1488530
Alternate Identifier(s):
OSTI ID: 1492749; OSTI ID: 1513397
Grant/Contract Number:  
NA0003763; AC02-05CH11231; AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 58; Journal Issue: 6; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
77 NANOSCIENCE AND NANOTECHNOLOGY; 38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; hydrogen-bonded organic frameworks; porous molecular solids; Crystal engineering; interpenetration isomerism; supramolecular chemistry

Citation Formats

Li, Penghao, Li, Peng, Ryder, Matthew R., Liu, Zhichang, Stern, Charlotte L., Farha, Omar K., and Stoddart, Fraser. “Interpenetration Isomerism” of Triptycene-Based Hydrogen-Bonded Organic Frameworks. United States: N. p., 2018. Web. doi:10.1002/anie.201811263.
Li, Penghao, Li, Peng, Ryder, Matthew R., Liu, Zhichang, Stern, Charlotte L., Farha, Omar K., & Stoddart, Fraser. “Interpenetration Isomerism” of Triptycene-Based Hydrogen-Bonded Organic Frameworks. United States. doi:10.1002/anie.201811263.
Li, Penghao, Li, Peng, Ryder, Matthew R., Liu, Zhichang, Stern, Charlotte L., Farha, Omar K., and Stoddart, Fraser. Tue . "“Interpenetration Isomerism” of Triptycene-Based Hydrogen-Bonded Organic Frameworks". United States. doi:10.1002/anie.201811263. https://www.osti.gov/servlets/purl/1488530.
@article{osti_1488530,
title = {“Interpenetration Isomerism” of Triptycene-Based Hydrogen-Bonded Organic Frameworks},
author = {Li, Penghao and Li, Peng and Ryder, Matthew R. and Liu, Zhichang and Stern, Charlotte L. and Farha, Omar K. and Stoddart, Fraser},
abstractNote = {In this work, we describe an example of “interpenetration isomerism” in three-dimensional (3D) hydrogen-bonded organic frameworks (HOFs). By exploiting the crystallization conditions for a peripherally extended triptycene H6PET, we can modulate the interpenetration of the assembled frameworks, yielding a two-fold interpenetrated structure PETHOF-1 (acs-2c topology) and a five-fold interpenetrated structure PETHOF-2 (acs-5c topology) as “interpenetration isomers”. In PETHOF-1, two individual nets are related by inversion symmetry and form an interwoven topology with a strikingly 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. Additionally, the activated materials show permanent porosity with high Brunauer–Emmett–Teller (BET) areas exceeding 1100 m2•g-1. Finally, we believe that synthetic control over the framework interpenetration can serve as a new design strategy to construct diverse and complex supramolecular architectures from simple organic building blocks.},
doi = {10.1002/anie.201811263},
journal = {Angewandte Chemie (International Edition)},
number = 6,
volume = 58,
place = {United States},
year = {2018},
month = {12}
}

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Cited by: 18 works
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    Works referencing / citing this record:

    How Interpenetration Ensures Rigidity and Permanent Porosity in a Highly Flexible Hybrid Solid
    journal, June 2012

    • Dan-Hardi, Meenakshi; Chevreau, Hubert; Devic, Thomas
    • Chemistry of Materials, Vol. 24, Issue 13
    • DOI: 10.1021/cm300450x

    Porous Organic Molecular Frameworks with Extrinsic Porosity: A Platform for Carbon Storage and Separation
    journal, July 2016


    Negative Thermal Expansion in the Metal-Organic Framework Material Cu 3 (1,3,5-benzenetricarboxylate) 2
    journal, November 2008

    • Wu, Yue; Kobayashi, Atsushi; Halder, Gregory J.
    • Angewandte Chemie International Edition, Vol. 47, Issue 46
    • DOI: 10.1002/anie.200803925

    Covalent organic frameworks: a materials platform for structural and functional designs
    journal, September 2016


    Understanding and Controlling the Dielectric Response of Metal-Organic Frameworks
    journal, March 2018

    • Ryder, Matthew R.; Donà, Lorenzo; Vitillo, Jenny G.
    • ChemPlusChem, Vol. 83, Issue 4
    • DOI: 10.1002/cplu.201700558

    Interpenetrated Three-Dimensional Networks of Hydrogen-Bonded Organic Species: A Systematic Analysis of the Cambridge Structural Database
    journal, February 2008

    • Baburin, Igor A.; Blatov, Vladislav A.; Carlucci, Lucia
    • Crystal Growth & Design, Vol. 8, Issue 2
    • DOI: 10.1021/cg0705660

    An Ultra-Robust and Crystalline Redeemable Hydrogen-Bonded Organic Framework for Synergistic Chemo-Photodynamic Therapy
    journal, June 2018

    • Yin, Qi; Zhao, Peng; Sa, Rong-Jian
    • Angewandte Chemie International Edition, Vol. 57, Issue 26
    • DOI: 10.1002/anie.201800354

    A Series of Layered Assemblies of Hydrogen-Bonded, Hexagonal Networks of C 3 -Symmetric π-Conjugated Molecules: A Potential Motif of Porous Organic Materials
    journal, May 2016

    • Hisaki, Ichiro; Nakagawa, Shoichi; Ikenaka, Nobuaki
    • Journal of the American Chemical Society, Vol. 138, Issue 20
    • DOI: 10.1021/jacs.6b02968

    A Hydrogen-Bonded Hexagonal Buckybowl Framework
    journal, October 2017

    • Hisaki, Ichiro; Toda, Hideaki; Sato, Hiroyasu
    • Angewandte Chemie International Edition, Vol. 56, Issue 48
    • DOI: 10.1002/anie.201708115

    Novel triptycene-derived hosts: synthesis and their applications in supramolecular chemistry
    journal, January 2011


    Supramolekulare Synthone für das Kristall-Engineering - eine neue organische Synthese
    journal, November 1995


    A Flexible Microporous Hydrogen-Bonded Organic Framework for Gas Sorption and Separation
    journal, July 2015

    • Wang, Hailong; Li, Bin; Wu, Hui
    • Journal of the American Chemical Society, Vol. 137, Issue 31
    • DOI: 10.1021/jacs.5b05644

    Deconstruction of Crystalline Networks into Underlying Nets: Relevance for Terminology Guidelines and Crystallographic Databases
    journal, May 2018

    • Bonneau, Charlotte; O’Keeffe, Michael; Proserpio, Davide M.
    • Crystal Growth & Design, Vol. 18, Issue 6
    • DOI: 10.1021/acs.cgd.8b00126

    BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions
    journal, March 1990

    • van der Sluis, P.; Spek, A. L.
    • Acta Crystallographica Section A Foundations of Crystallography, Vol. 46, Issue 3
    • DOI: 10.1107/s0108767389011189

    Molecular Tectonics. Porous Hydrogen-Bonded Networks Built from Derivatives of 9,9‘-Spirobifluorene
    journal, March 2004

    • Fournier, Jean-Hugues; Maris, Thierry; Wuest, James D.
    • The Journal of Organic Chemistry, Vol. 69, Issue 6
    • DOI: 10.1021/jo0348118

    Molecular Tectonics. Selective Exchange of Cations in Porous Anionic Hydrogen-Bonded Networks Built from Derivatives of Tetraphenylborate
    journal, April 2005

    • Malek, Nadia; Maris, Thierry; Simard, Michel
    • Journal of the American Chemical Society, Vol. 127, Issue 16
    • DOI: 10.1021/ja042233m

    Double−Step Gas Sorption of a Two−Dimensional Metal−Organic Framework
    journal, October 2007

    • Kondo, Atsushi; Noguchi, Hiroshi; Carlucci, Lucia
    • Journal of the American Chemical Society, Vol. 129, Issue 41
    • DOI: 10.1021/ja073568h

    From Molecules to Crystal Engineering:  Supramolecular Isomerism and Polymorphism in Network Solids
    journal, June 2001

    • Moulton, Brian; Zaworotko, Michael J.
    • Chemical Reviews, Vol. 101, Issue 6
    • DOI: 10.1021/cr9900432

    The role of reticular chemistry in the design of CO2 reduction catalysts
    journal, February 2018


    An Ultrastable and Easily Regenerated Hydrogen-Bonded Organic Molecular Framework with Permanent Porosity
    journal, January 2017


    Rationale Herstellung eines extrinsisch porösen Molekülkristalls mit einer außergewöhnlich großen spezifischen Oberfläche
    journal, March 2012


    Dissecting Porosity in Molecular Crystals: Influence of Geometry, Hydrogen Bonding, and [π···π] Stacking on the Solid-State Packing of Fluorinated Aromatics
    journal, April 2018

    • Hashim, Mohamed I.; Le, Ha T. M.; Chen, Teng-Hao
    • Journal of the American Chemical Society, Vol. 140, Issue 18
    • DOI: 10.1021/jacs.8b02869

    Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
    journal, November 1995

    • Desiraju, Gautam R.
    • Angewandte Chemie International Edition in English, Vol. 34, Issue 21
    • DOI: 10.1002/anie.199523111

    Function-led design of new porous materials
    journal, May 2015


    Isomerism in Metal–Organic Frameworks: “Framework Isomers”
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