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Title: Redox-switchable breathing behavior in tetrathiafulvalene-based metal–organic frameworks

Abstract

Metal–organic frameworks (MOFs) that respond to external stimuli such as guest molecules, temperature, or redox conditions are highly desirable. Herein, we coupled redox-switchable properties with breathing behavior induced by guest molecules in a single framework. Guided by topology, two flexible isomeric MOFs, compounds 1 and 2, with a formula of In(Me 2NH 2) (TTFTB), were constructed via a combination of [In(COO) 4]- metal nodes and tetratopic tetrathiafulvalene-based linkers (TTFTB). The two compounds show different breathing behaviors upon the introduction of N 2. Single-crystal X-ray diffraction, accompanied by molecular simulations, reveals that the breathing mechanism of 1 involves the bending of metal–ligand bonds and the sliding of interpenetrated frameworks, while 2 undergoes simple distortion of linkers. Reversible oxidation and reduction of TTF moieties changes the linker flexibility, which in turn switches the breathing behavior of 2. The redox-switchable breathing behavior can potentially be applied to the design of stimuli-responsive MOFs.

Authors:
 [1];  [2];  [1]; ORCiD logo [2];  [1];  [2];  [2];  [2]; ORCiD logo [1]; ORCiD logo [2]
+ Show Author Affiliations
  1. Nanjing Univ. (China)
  2. Texas A & M Univ., College Station, TX (United States)
Publication Date:
Research Org.:
Univ. of Texas, Austin, TX (United States). Energy Frontier Research Center (EFRC)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1470031
Grant/Contract Number:  
EE0007049; FE0026472; SC0001015
Resource Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 8; Journal Issue: 1; Related Information: CGS partners with University of California, Berkeley; University of California, Davis; Lawrence Berkeley National Laboratory; University of Minnesota; National Energy Technology Laboratory; Texas A&M University; Journal ID: ISSN 2041-1723
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
membrane; carbon capture; materials and chemistry by design; synthesis (novel materials); synthesis (self-assembly); synthesis (scalable processing)

Citation Formats

Su, Jian, Yuan, Shuai, Wang, Hai-Ying, Huang, Lan, Ge, Jing-Yuan, Joseph, Elizabeth, Qin, Junsheng, Cagin, Tahir, Zuo, Jing-Lin, and Zhou, Hong-Cai. Redox-switchable breathing behavior in tetrathiafulvalene-based metal–organic frameworks. United States: N. p., 2017. Web. doi:10.1038/s41467-017-02256-y.
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Su, Jian, Yuan, Shuai, Wang, Hai-Ying, Huang, Lan, Ge, Jing-Yuan, Joseph, Elizabeth, Qin, Junsheng, Cagin, Tahir, Zuo, Jing-Lin, & Zhou, Hong-Cai. Redox-switchable breathing behavior in tetrathiafulvalene-based metal–organic frameworks. United States. doi:10.1038/s41467-017-02256-y.
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Su, Jian, Yuan, Shuai, Wang, Hai-Ying, Huang, Lan, Ge, Jing-Yuan, Joseph, Elizabeth, Qin, Junsheng, Cagin, Tahir, Zuo, Jing-Lin, and Zhou, Hong-Cai. Fri . "Redox-switchable breathing behavior in tetrathiafulvalene-based metal–organic frameworks". United States. doi:10.1038/s41467-017-02256-y. https://www.osti.gov/servlets/purl/1470031.
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@article{osti_1470031,
title = {Redox-switchable breathing behavior in tetrathiafulvalene-based metal–organic frameworks},
author = {Su, Jian and Yuan, Shuai and Wang, Hai-Ying and Huang, Lan and Ge, Jing-Yuan and Joseph, Elizabeth and Qin, Junsheng and Cagin, Tahir and Zuo, Jing-Lin and Zhou, Hong-Cai},
abstractNote = {Metal–organic frameworks (MOFs) that respond to external stimuli such as guest molecules, temperature, or redox conditions are highly desirable. Herein, we coupled redox-switchable properties with breathing behavior induced by guest molecules in a single framework. Guided by topology, two flexible isomeric MOFs, compounds 1 and 2, with a formula of In(Me2NH2) (TTFTB), were constructed via a combination of [In(COO)4]- metal nodes and tetratopic tetrathiafulvalene-based linkers (TTFTB). The two compounds show different breathing behaviors upon the introduction of N2. Single-crystal X-ray diffraction, accompanied by molecular simulations, reveals that the breathing mechanism of 1 involves the bending of metal–ligand bonds and the sliding of interpenetrated frameworks, while 2 undergoes simple distortion of linkers. Reversible oxidation and reduction of TTF moieties changes the linker flexibility, which in turn switches the breathing behavior of 2. The redox-switchable breathing behavior can potentially be applied to the design of stimuli-responsive MOFs.},
doi = {10.1038/s41467-017-02256-y},
journal = {Nature Communications},
number = 1,
volume = 8,
place = {United States},
year = {2017},
month = {12}
}
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DOI:  10.1038/s41467-017-02256-y
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Cited by: 15 works
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Figures / Tables:

Fig. 1 Fig. 1: Topology-guided design of compounds 1 and 2. a [In(COO)4]− inorganic building unit as a tetrahedral node; b TTFTB organic linker as a square planar node; c pts topology; d, e two networks derived from pts topology; f, g structure of compounds 1 and 2. Color scheme: In, cyan;more » O, red; C, gray; S, yellow« less
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Works referenced in this record:

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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
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    Works referencing / citing this record:

    How Hydration Drastically Improves Adsorption Selectivity for CO2 over CH4 in the Flexible Chromium Terephthalate MIL-53
    journal, November 2006

    • Llewellyn, Philip L.; Bourrelly, Sandrine; Serre, Christian
    • Angewandte Chemie, Vol. 118, Issue 46
    • DOI: 10.1002/ange.200602278

    Electrically Conductive Porous Metal-Organic Frameworks
    journal, January 2016

    • Sun, Lei; Campbell, Michael G.; Dincă, Mircea
    • Angewandte Chemie International Edition, Vol. 55, Issue 11
    • DOI: 10.1002/anie.201506219

    Photo- and Electronically Switchable Spin-Crossover Iron(II) Metal-Organic Frameworks Based on a Tetrathiafulvalene Ligand
    journal, April 2017

    • Wang, Hai-Ying; Ge, Jing-Yuan; Hua, Carol
    • Angewandte Chemie International Edition, Vol. 56, Issue 20
    • DOI: 10.1002/anie.201611824

    Lock-and-Key and Shape-Memory Effects in an Unconventional Synthetic Path to Magnesium Metal-Organic Frameworks
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    • Yang, Huajun; Trieu, Thuong Xinh; Zhao, Xiang
    • Angewandte Chemie International Edition, Vol. 58, Issue 34
    • DOI: 10.1002/anie.201905876

    Stimulus-Responsive Metal-Organic Frameworks
    journal, May 2014

    • Nagarkar, Sanjog S.; Desai, Aamod V.; Ghosh, Sujit K.
    • Chemistry - An Asian Journal, Vol. 9, Issue 9
    • DOI: 10.1002/asia.201402004

    Microporous Organically Pillared Layered Silicates (MOPS): A Versatile Class of Functional Porous Materials
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    • Rieß, Martin; Senker, Jürgen; Schobert, Rainer
    • Chemistry - A European Journal, Vol. 25, Issue 9
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    Electronic, Structural and Functional Versatility in Tetrathiafulvalene‐Lanthanide Metal–Organic Frameworks
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    Novel Topology in Semiconducting Tetrathiafulvalene Lanthanide Metal-Organic Frameworks
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    Functional coordination polymers based on redox-active tetrathiafulvalene and its derivatives
    journal, August 2017

    Flexible microporous coordination polymers
    journal, August 2005

    • Uemura, Kazuhiro; Matsuda, Ryotaro; Kitagawa, Susumu
    • Journal of Solid State Chemistry, Vol. 178, Issue 8
    • DOI: 10.1016/j.jssc.2005.05.036

    Metal–Organic Framework Materials as Chemical Sensors
    journal, September 2011

    • Kreno, Lauren E.; Leong, Kirsty; Farha, Omar K.
    • Chemical Reviews, Vol. 112, Issue 2, p. 1105-1125
    • DOI: 10.1021/cr200324t

    Introduction to Metal–Organic Frameworks
    journal, September 2011

    • Zhou, Hong-Cai; Long, Jeffrey R.; Yaghi, Omar M.
    • Chemical Reviews, Vol. 112, Issue 2, p. 673-674
    • DOI: 10.1021/cr300014x

    Topological Analysis of Metal–Organic Frameworks with Polytopic Linkers and/or Multiple Building Units and the Minimal Transitivity Principle
    journal, November 2013

    • Li, Mian; Li, Dan; O’Keeffe, Michael
    • Chemical Reviews, Vol. 114, Issue 2
    • DOI: 10.1021/cr400392k

    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
    • DOI: 10.1021/ja0276974

    Guest-to-Host Transmission of Structural Changes for Stimuli-Responsive Adsorption Property
    journal, March 2012

    • Yanai, Nobuhiro; Uemura, Takashi; Inoue, Masafumi
    • Journal of the American Chemical Society, Vol. 134, Issue 10
    • DOI: 10.1021/ja2115713

    High Charge Mobility in a Tetrathiafulvalene-Based Microporous Metal–Organic Framework
    journal, July 2012

    • Narayan, Tarun C.; Miyakai, Tomoyo; Seki, Shu
    • Journal of the American Chemical Society, Vol. 134, Issue 31
    • DOI: 10.1021/ja3059827

    Elucidating the Breathing of the Metal–Organic Framework MIL-53(Sc) with ab Initio Molecular Dynamics Simulations and in Situ X-ray Powder Diffraction Experiments
    journal, June 2013

    • Chen, Linjiang; Mowat, John P. S.; Fairen-Jimenez, David
    • Journal of the American Chemical Society, Vol. 135, Issue 42
    • DOI: 10.1021/ja403453g

    On the Flexibility of Metal–Organic Frameworks
    journal, January 2014

    • Sarkisov, Lev; Martin, Richard L.; Haranczyk, Maciej
    • Journal of the American Chemical Society, Vol. 136, Issue 6
    • DOI: 10.1021/ja411673b

    Cation-Dependent Intrinsic Electrical Conductivity in Isostructural Tetrathiafulvalene-Based Microporous Metal–Organic Frameworks
    journal, January 2015

    • Park, Sarah S.; Hontz, Eric R.; Sun, Lei
    • Journal of the American Chemical Society, Vol. 137, Issue 5
    • DOI: 10.1021/ja512437u

    A Reversible Crystallinity-Preserving Phase Transition in Metal–Organic Frameworks: Discovery, Mechanistic Studies, and Potential Applications
    journal, June 2015

    • Liu, Dahuan; Liu, Tian-Fu; Chen, Ying-Pin
    • Journal of the American Chemical Society, Vol. 137, Issue 24
    • DOI: 10.1021/jacs.5b02999

    Incorporation of Fused Tetrathiafulvalenes (TTFs) into Polythiophene Architectures:  Varying the Electroactive Dominance of the TTF Species in Hybrid Systems
    journal, February 2006

    • Berridge, Rory; Skabara, Peter J.; Pozo-Gonzalo, Cristina
    • The Journal of Physical Chemistry B, Vol. 110, Issue 7
    • DOI: 10.1021/jp057256h

    On the Thermodynamics of Framework Breathing: A Free Energy Model for Gas Adsorption in MIL-53
    journal, May 2013

    • Ghysels, An; Vanduyfhuys, Louis; Vandichel, Matthias
    • The Journal of Physical Chemistry C, Vol. 117, Issue 22
    • DOI: 10.1021/jp311601q

    Synthesis and Doping of a Multifunctional Tetrathiafulvalene- Substituted Poly(isocyanide)
    journal, October 2007

    • Gomar-Nadal, Elba; Mugica, Laurent; Vidal-Gancedo, José
    • Macromolecules, Vol. 40, Issue 21
    • DOI: 10.1021/ma0710986

    X-ray analysis on the nanogram to microgram scale using porous complexes
    journal, March 2013

    • Inokuma, Yasuhide; Yoshioka, Shota; Ariyoshi, Junko
    • Nature, Vol. 495, Issue 7442
    • DOI: 10.1038/nature11990

    Cooperative insertion of CO2 in diamine-appended metal-organic frameworks
    journal, March 2015

    • McDonald, Thomas M.; Mason, Jarad A.; Kong, Xueqian
    • Nature, Vol. 519, Issue 7543
    • DOI: 10.1038/nature14327

    Methane storage in flexible metal–organic frameworks with intrinsic thermal management
    journal, October 2015

    • Mason, Jarad A.; Oktawiec, Julia; Taylor, Mercedes K.
    • Nature, Vol. 527, Issue 7578
    • DOI: 10.1038/nature15732

    Capturing snapshots of post-synthetic metallation chemistry in metal–organic frameworks
    journal, September 2014

    • Bloch, Witold M.; Burgun, Alexandre; Coghlan, Campbell J.
    • Nature Chemistry, Vol. 6, Issue 10
    • DOI: 10.1038/nchem.2045

    Solvent-switchable continuous-breathing behaviour in a diamondoid metal–organic framework and its influence on CO2 versus CH4 selectivity
    journal, March 2017

    • Carrington, Elliot J.; McAnally, Craig A.; Fletcher, Ashleigh J.
    • Nature Chemistry, Vol. 9, Issue 9
    • DOI: 10.1038/nchem.2747

    Soft porous crystals
    journal, November 2009

    • Horike, Satoshi; Shimomura, Satoru; Kitagawa, Susumu
    • Nature Chemistry, Vol. 1, Issue 9, p. 695-704
    • DOI: 10.1038/nchem.444

    Metal–organic framework materials as catalysts
    journal, January 2009

    • Lee, JeongYong; Farha, Omar K.; Roberts, John
    • Chemical Society Reviews, Vol. 38, Issue 5, p. 1450-1459
    • DOI: 10.1039/b807080f

    The pervasive chemistry of metal–organic frameworks
    journal, January 2009

    • Long, Jeffrey R.; Yaghi, Omar M.
    • Chemical Society Reviews, Vol. 38, Issue 5, p. 1213-1214
    • DOI: 10.1039/b903811f

    Methane storage in advanced porous materials
    journal, January 2012

    • Makal, Trevor A.; Li, Jian-Rong; Lu, Weigang
    • Chemical Society Reviews, Vol. 41, Issue 23
    • DOI: 10.1039/c2cs35251f

    Turning on the flexibility of isoreticular porous coordination frameworks for drastically tunable framework breathing and thermal expansion
    journal, January 2013

    • Wei, Yong-Sheng; Chen, Kai-Jie; Liao, Pei-Qin
    • Chemical Science, Vol. 4, Issue 4
    • DOI: 10.1039/c3sc22222e

    Nanopore-induced host–guest charge transfer phenomena in a metal–organic framework
    journal, January 2018

    • Yamamoto, S.; Pirillo, J.; Hijikata, Y.
    • Chemical Science, Vol. 9, Issue 13
    • DOI: 10.1039/c7sc05390h

    C–C to CC conversion within a supramolecular framework of tetrathiafulvalene: a confinement effect and an oxygen related dehydrogenation
    journal, January 2018

    • Zhang, Ping; Huo, Peng; Zhang, Xuan
    • Chemical Communications, Vol. 54, Issue 53
    • DOI: 10.1039/c8cc03197e

    Tetrathiopyridyl-tetrathiafulvalene-based Cd( ii ) coordination polymers: one ligand, one metal cation, many possibilities
    journal, January 2019

    • Bechu, Damien; Rogez, Guillaume; Hosseini, Mir Wais
    • New Journal of Chemistry, Vol. 43, Issue 36
    • DOI: 10.1039/c9nj03572a

    Redox-active metal–organic frameworks for energy conversion and storage
    journal, January 2019

    • Calbo, Joaquín; Golomb, Matthias J.; Walsh, Aron
    • Journal of Materials Chemistry A, Vol. 7, Issue 28
    • DOI: 10.1039/c9ta04680a

    Role of Solvent-Host Interactions That Lead to Very Large Swelling of Hybrid Frameworks
    journal, March 2007

    Self-Accelerating CO Sorption in a Soft Nanoporous Crystal
    journal, December 2013

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