skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

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 H6PET, 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 m2 g-1. Synthetic control over the framework interpenetration could serve as a new strategy to construct 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.:
University of Notre Dame, IN (United States); Oak Ridge National Laboratory (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:
Journal Article: Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
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. https://doi.org/10.1002/anie.201811263
Li, Penghao, Li, Peng, Ryder, Matthew R., Liu, Zhichang, Stern, Charlotte L., Farha, Omar K., and Stoddart, Fraser. 2018. "“Interpenetration Isomerism” of Triptycene-Based Hydrogen-Bonded Organic Frameworks". United States. https://doi.org/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 = {We describe an example of “interpenetration isomerism” in three-dimensional hydrogen-bonded organic frameworks. 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 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 m2 g-1. Synthetic control over the framework interpenetration could serve as a new strategy to construct complex supramolecular architectures from simple organic building blocks.},
doi = {10.1002/anie.201811263},
url = {https://www.osti.gov/biblio/1488530}, journal = {Angewandte Chemie (International Edition)},
issn = {1433-7851},
number = 6,
volume = 58,
place = {United States},
year = {Tue Dec 11 00:00:00 EST 2018},
month = {Tue Dec 11 00:00:00 EST 2018}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 75 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

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


A Robust Binary Supramolecular Organic Framework (SOF) with High CO 2 Adsorption and Selectivity
journal, September 2014


Two solvent-induced porous hydrogen-bonded organic frameworks: solvent effects on structures and functionalities
journal, January 2017


Catenated and non-catenated inclusion complexes of trimesic acid
journal, April 1987


Activation of metal–organic framework materials
journal, January 2013


Engineering crystals by the strategy of molecular tectonics
journal, January 2005


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


Docking Strategy To Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area
journal, July 2018


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


Crystal Engineering: From Molecule to Crystal
journal, June 2013


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


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


Selective CO 2 Adsorption in a Supramolecular Organic Framework
journal, March 2016


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


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


A Hydrogen-Bonded Hexagonal Buckybowl Framework
journal, October 2017


Interpenetration control in metal–organic frameworks for functional applications
journal, August 2013


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


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


Very Large Breathing Effect in the First Nanoporous Chromium(III)-Based Solids MIL-53 or CrIII(OH)·{O2C−C6H4−CO2}·{HO2C−C6H4−CO2H}x·H2Oy
journal, November 2002

  • 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

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


Selective CO 2 Adsorption in a Supramolecular Organic Framework
journal, March 2016


A Hydrogen-Bonded Hexagonal Buckybowl Framework
journal, October 2017


Metal–Organic Frameworks as Platforms for Functional Materials
journal, February 2016


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


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


Isomerism in Metal–Organic Frameworks: “Framework Isomers”
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
journal, May 2016


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


Engineering Hydrogen-Bonded Molecular Crystals Built from Derivatives of Hexaphenylbenzene and Related Compounds
journal, April 2007


Docking Strategy To Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area
journal, July 2018


A Solid-State Chemist's View of the Crystal Polymorphism of Organic Compounds
journal, September 2007


A C 3 -Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals
journal, January 2015


A permanently porous single molecule H-bonded organic framework for selective CO 2 capture
journal, January 2016


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


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


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


Introduction to Metal–Organic Frameworks
journal, September 2011


Observation of Interpenetration Isomerism in Covalent Organic Frameworks
journal, April 2018


Exceptional Thermal Stability in a Supramolecular Organic Framework: Porosity and Gas Storage
journal, October 2010


Thermally robust and porous noncovalent organic framework with high affinity for fluorocarbons and CFCs
journal, October 2014


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


The atom, the molecule, and the covalent organic framework
journal, March 2017


A Homochiral Microporous Hydrogen-Bonded Organic Framework for Highly Enantioselective Separation of Secondary Alcohols
journal, January 2014


A Molecular Propeller with Three Nanohoop Blades: Synthesis, Characterization, and Solid-State Packing
journal, April 2017


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


Applied Topological Analysis of Crystal Structures with the Program Package ToposPro
journal, May 2014


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


Rational Construction of an Extrinsic Porous Molecular Crystal with an Extraordinary High Specific Surface Area
journal, March 2012


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


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


Single-crystal structure validation with the program PLATON
journal, January 2003


A Molecular Propeller with Three Nanohoop Blades: Synthesis, Characterization, and Solid-State Packing
journal, April 2017


Supercritical Processing as a Route to High Internal Surface Areas and Permanent Microporosity in Metal−Organic Framework Materials
journal, January 2009


A Microporous Hydrogen-Bonded Organic Framework for Highly Selective C 2 H 2 /C 2 H 4 Separation at Ambient Temperature
journal, September 2011


Grand Challenges and Future Opportunities for Metal–Organic Frameworks
journal, June 2017


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


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


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


A C 3 -Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals
journal, February 2015


Predictably Ordered Open Hydrogen-Bonded Networks Built from Indeno[1,2- b ]fluorenes
journal, July 2017


Works referencing / citing this record:

Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity
journal, May 2019


Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity
journal, August 2019


Molecular Tectonics: A Node‐and‐Linker Building Block Approach to a Family of Hydrogen‐Bonded Frameworks
journal, July 2019


Controlled Growth of Ag Nanocrystals in a H‐Bonded Open Framework
journal, September 2019


Hydrogen-bonded porous frameworks constructed by rigid π-conjugated molecules with carboxy groups
journal, January 2020


Optically active triptycenes containing hexa- peri -hexabenzocoronene units
journal, January 2019


A ferrocene-templated Pd-bearing molecular reactor
journal, January 2020


A nonconventional host–guest cubic assembly based on γ-cyclodextrin and a Keggin-type polyoxometalate
journal, January 2020


Balancing volumetric and gravimetric uptake in highly porous materials for clean energy
journal, April 2020