DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Diverse π–π stacking motifs modulate electrical conductivity in tetrathiafulvalene-based metal–organic frameworks

Abstract

We report three electrically conductive metal–organic frameworks (MOFs) based on a tetrathiafulvalene linker and La 3+ .

Authors:
ORCiD logo [1]; ORCiD logo [2];  [1]; ORCiD logo [3]; ORCiD logo [1]
  1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, USA
  2. Samara Center for Theoretical Material Science (SCTMS), Samara State Technical University, Samara, Russia, SCTMS
  3. Samara Center for Theoretical Material Science (SCTMS), Samara State Technical University, Samara, Russia, Dipartimento di Chimica
Publication Date:
Research Org.:
Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1547669
Alternate Identifier(s):
OSTI ID: 1601983
Grant/Contract Number:  
SC0018235
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 10 Journal Issue: 37; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Xie, Lilia S., Alexandrov, Eugeny V., Skorupskii, Grigorii, Proserpio, Davide M., and Dincă, Mircea. Diverse π–π stacking motifs modulate electrical conductivity in tetrathiafulvalene-based metal–organic frameworks. United Kingdom: N. p., 2019. Web. doi:10.1039/C9SC03348C.
Xie, Lilia S., Alexandrov, Eugeny V., Skorupskii, Grigorii, Proserpio, Davide M., & Dincă, Mircea. Diverse π–π stacking motifs modulate electrical conductivity in tetrathiafulvalene-based metal–organic frameworks. United Kingdom. https://doi.org/10.1039/C9SC03348C
Xie, Lilia S., Alexandrov, Eugeny V., Skorupskii, Grigorii, Proserpio, Davide M., and Dincă, Mircea. Wed . "Diverse π–π stacking motifs modulate electrical conductivity in tetrathiafulvalene-based metal–organic frameworks". United Kingdom. https://doi.org/10.1039/C9SC03348C.
@article{osti_1547669,
title = {Diverse π–π stacking motifs modulate electrical conductivity in tetrathiafulvalene-based metal–organic frameworks},
author = {Xie, Lilia S. and Alexandrov, Eugeny V. and Skorupskii, Grigorii and Proserpio, Davide M. and Dincă, Mircea},
abstractNote = {We report three electrically conductive metal–organic frameworks (MOFs) based on a tetrathiafulvalene linker and La 3+ .},
doi = {10.1039/C9SC03348C},
journal = {Chemical Science},
number = 37,
volume = 10,
place = {United Kingdom},
year = {Wed Sep 25 00:00:00 EDT 2019},
month = {Wed Sep 25 00:00:00 EDT 2019}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C9SC03348C

Citation Metrics:
Cited by: 102 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal−Organic Carboxylate Frameworks
journal, April 2001

  • Eddaoudi, Mohamed; Moler, David B.; Li, Hailian
  • Accounts of Chemical Research, Vol. 34, Issue 4, p. 319-330
  • DOI: 10.1021/ar000034b

Doping Metal–Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis
journal, August 2011

  • Wang, Cheng; Xie, Zhigang; deKrafft, Kathryn E.
  • Journal of the American Chemical Society, Vol. 133, Issue 34, p. 13445-13454
  • DOI: 10.1021/ja203564w

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

Redox Activities of Metal–Organic Frameworks Incorporating Rare-Earth Metal Chains and Tetrathiafulvalene Linkers
journal, February 2019


Blue photoluminescent 3D Zn(II) metal-organic framework constructing from pyridine-2,4,6-tricarboxylate
journal, August 2008


The Reticular Chemistry Structure Resource (RCSR) Database of, and Symbols for, Crystal Nets
journal, December 2008

  • O’Keeffe, Michael; Peskov, Maxim A.; Ramsden, Stuart J.
  • Accounts of Chemical Research, Vol. 41, Issue 12, p. 1782-1789
  • DOI: 10.1021/ar800124u

Is iron unique in promoting electrical conductivity in MOFs?
journal, January 2017

  • Sun, Lei; Hendon, Christopher H.; Park, Sarah S.
  • Chemical Science, Vol. 8, Issue 6
  • DOI: 10.1039/C7SC00647K

A spectroscopic and electrochemical investigation of a tetrathiafulvalene series of metal–organic frameworks
journal, November 2018


Selective Vapor Pressure Dependent Proton Transport in a Metal–Organic Framework with Two Distinct Hydrophilic Pores
journal, February 2018

  • Park, Sarah S.; Rieth, Adam J.; Hendon, Christopher H.
  • Journal of the American Chemical Society, Vol. 140, Issue 6
  • DOI: 10.1021/jacs.7b12784

A Guest-Responsive Fluorescent 3D Microporous Metal−Organic Framework Derived from a Long-Lifetime Pyrene Core
journal, March 2010

  • Stylianou, Kyriakos C.; Heck, Romain; Chong, Samantha Y.
  • Journal of the American Chemical Society, Vol. 132, Issue 12, p. 4119-4130
  • DOI: 10.1021/ja906041f

Electronic, Structural and Functional Versatility in Tetrathiafulvalene‐Lanthanide Metal–Organic Frameworks
journal, August 2019

  • Castells‐Gil, Javier; Mañas‐Valero, Samuel; Vitórica‐Yrezábal, Iñigo J.
  • Chemistry – A European Journal, Vol. 25, Issue 54
  • DOI: 10.1002/chem.201902855

Reticular synthesis and the design of new materials
journal, June 2003

  • Yaghi, Omar M.; O'Keeffe, Michael; Ockwig, Nathan W.
  • Nature, Vol. 423, Issue 6941, p. 705-714
  • DOI: 10.1038/nature01650

Luminescent Functional Metal–Organic Frameworks
journal, June 2011

  • Cui, Yuanjing; Yue, Yanfeng; Qian, Guodong
  • Chemical Reviews, Vol. 112, Issue 2
  • DOI: 10.1021/cr200101d

Hydrogen storage in metal–organic frameworks
journal, January 2009

  • Murray, Leslie J.; Dincă, Mircea; Long, Jeffrey R.
  • Chemical Society Reviews, Vol. 38, Issue 5, p. 1294-1314
  • DOI: 10.1039/b802256a

Tunable Mixed-Valence Doping toward Record Electrical Conductivity in a Three-Dimensional Metal–Organic Framework
journal, May 2018

  • Xie, Lilia S.; Sun, Lei; Wan, Ruomeng
  • Journal of the American Chemical Society, Vol. 140, Issue 24
  • DOI: 10.1021/jacs.8b03604

Metal–Organic Frameworks as Active Materials in Electronic Sensor Devices
journal, May 2017


Synthesis and Structure of (ET)[Ni{SC(CN)?C(CN)S}2], a Radical Cation Salt of Bis(ethylenedithio)tetrathiafulvalene
journal, May 1988

  • Reith, Walter; Polborn, Kurt; Amberger, Eberhard
  • Angewandte Chemie International Edition in English, Vol. 27, Issue 5
  • DOI: 10.1002/anie.198806991

The role of temperature in the synthesis of hybrid inorganic–organic materials: the example of cobalt succinates
journal, January 2004

  • Forster, Paul M.; Burbank, Andrea R.; Livage, Carine
  • Chem. Commun., Issue 4
  • DOI: 10.1039/B311156C

Redox-switchable breathing behavior in tetrathiafulvalene-based metal–organic frameworks
journal, December 2017


Breathing-Dependent Redox Activity in a Tetrathiafulvalene-Based Metal–Organic Framework
journal, July 2018

  • Souto, Manuel; Romero, Jorge; Calbo, Joaquín
  • Journal of the American Chemical Society, Vol. 140, Issue 33
  • DOI: 10.1021/jacs.8b05890

Novel Topology in Semiconducting Tetrathiafulvalene Lanthanide Metal-Organic Frameworks
journal, August 2018


The Organic Secondary Building Unit: Strong Intermolecular π Interactions Define Topology in MIT-25, a Mesoporous MOF with Proton-Replete Channels
journal, March 2017

  • Park, Sarah S.; Hendon, Christopher H.; Fielding, Alistair J.
  • Journal of the American Chemical Society, Vol. 139, Issue 10
  • DOI: 10.1021/jacs.6b13176

Electrical conductivity and electroluminescence of a new anthracene-based metal–organic framework with π-conjugated zigzag chains
journal, January 2016

  • Chen, Dashu; Xing, Hongzhu; Su, Zhongmin
  • Chemical Communications, Vol. 52, Issue 10
  • DOI: 10.1039/C5CC09065B

An updated roadmap for the integration of metal–organic frameworks with electronic devices and chemical sensors
journal, January 2017

  • Stassen, Ivo; Burtch, Nicholas; Talin, Alec
  • Chemical Society Reviews, Vol. 46, Issue 11
  • DOI: 10.1039/C7CS00122C

Deconstructing the Crystal Structures of Metal–Organic Frameworks and Related Materials into Their Underlying Nets
journal, September 2011

  • O’Keeffe, Michael; Yaghi, Omar M.
  • Chemical Reviews, Vol. 112, Issue 2, p. 675-702
  • DOI: 10.1021/cr200205j

Secondary building units as the turning point in the development of the reticular chemistry of MOFs
journal, October 2018

  • Kalmutzki, Markus J.; Hanikel, Nikita; Yaghi, Omar M.
  • Science Advances, Vol. 4, Issue 10
  • DOI: 10.1126/sciadv.aat9180

Crystal and molecular structure of the aromatic sulphur compound 2,2′-bi-1,3-dithiole. Evidence for d-orbital participation in bonding
journal, January 1971

  • Cooper, W. F.; Kenny, N. C.; Edmonds, J. W.
  • J. Chem. Soc. D, Vol. 0, Issue 16
  • DOI: 10.1039/C29710000889

Tunable Rare Earth fcu -MOF Platform: Access to Adsorption Kinetics Driven Gas/Vapor Separations via Pore Size Contraction
journal, April 2015

  • Xue, Dong-Xu; Belmabkhout, Youssef; Shekhah, Osama
  • Journal of the American Chemical Society, Vol. 137, Issue 15
  • DOI: 10.1021/ja5131403

Distinguishing Metal–Organic Frameworks
journal, January 2018

  • Barthel, Senja; Alexandrov, Eugeny V.; Proserpio, Davide M.
  • Crystal Growth & Design, Vol. 18, Issue 3
  • DOI: 10.1021/acs.cgd.7b01663

Chemiresistive Sensor Arrays from Conductive 2D Metal–Organic Frameworks
journal, October 2015

  • Campbell, Michael G.; Liu, Sophie F.; Swager, Timothy M.
  • Journal of the American Chemical Society, Vol. 137, Issue 43
  • DOI: 10.1021/jacs.5b09600

The crystal structure of the 1:1 radical cation–radical anion salt of 2,2'-bis-l,3-dithiole (TTF) and 7,7,8,8-tetracyanoquinodimethane (TCNQ)
journal, March 1974

  • Kistenmacher, T. J.; Phillips, T. E.; Cowan, D. O.
  • Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 30, Issue 3
  • DOI: 10.1107/S0567740874003669

An EXAFS study of the formation of a nanoporous metal–organic framework: evidence for the retention of secondary building units during synthesis
journal, January 2006

  • Surblé, Suzy; Millange, Franck; Serre, Christian
  • Chemical Communications, Issue 14
  • DOI: 10.1039/b600709k

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

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

Secondary building units, nets and bonding in the chemistry of metal–organic frameworks
journal, January 2009

  • Tranchemontagne, David J.; Mendoza-Cortés, José L.; O’Keeffe, Michael
  • Chemical Society Reviews, Vol. 38, Issue 5, p. 1257-1283
  • DOI: 10.1039/b817735j

Charge Delocalization and Bulk Electronic Conductivity in the Mixed-Valence Metal–Organic Framework Fe(1,2,3-triazolate) 2 (BF 4 ) x
journal, June 2018

  • Park, Jesse G.; Aubrey, Michael L.; Oktawiec, Julia
  • Journal of the American Chemical Society, Vol. 140, Issue 27
  • DOI: 10.1021/jacs.8b03696

Charge Transport in Organic Semiconductors
journal, April 2007

  • Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A.
  • Chemical Reviews, Vol. 107, Issue 4
  • DOI: 10.1021/cr050140x

Electroactive Metalorganic Frameworks
journal, October 2018

  • Medina, Dana D.; Mähringer, Andre; Bein, Thomas
  • Israel Journal of Chemistry, Vol. 58, Issue 9-10
  • DOI: 10.1002/ijch.201800110

Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage
journal, January 2002

  • Eddaoudi, Mohamed; Kim, Jaheon; Rosi, Nathaniel
  • Science, Vol. 295, Issue 5554, p. 469-472
  • DOI: 10.1126/science.1067208

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

Rod Packings and Metal−Organic Frameworks Constructed from Rod-Shaped Secondary Building Units
journal, February 2005

  • Rosi, Nathaniel L.; Kim, Jaheon; Eddaoudi, Mohamed
  • Journal of the American Chemical Society, Vol. 127, Issue 5, p. 1504-1518
  • DOI: 10.1021/ja045123o

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

  • Blatov, Vladislav A.; Shevchenko, Alexander P.; Proserpio, Davide M.
  • Crystal Growth & Design, Vol. 14, Issue 7
  • DOI: 10.1021/cg500498k

Room-Temperature and Solution-State Observation of the Mixed-Valence Cation Radical Dimer of Tetrathiafulvalene, [(TTF) 2 ] +• , within a Self-Assembled Cage
journal, October 2005

  • Yoshizawa, Michito; Kumazawa, Kazuhisa; Fujita, Makoto
  • Journal of the American Chemical Society, Vol. 127, Issue 39
  • DOI: 10.1021/ja053508g

Cu 3 (hexaiminotriphenylene) 2 : An Electrically Conductive 2D Metal-Organic Framework for Chemiresistive Sensing
journal, February 2015

  • Campbell, Michael G.; Sheberla, Dennis; Liu, Sophie F.
  • Angewandte Chemie International Edition, Vol. 54, Issue 14
  • DOI: 10.1002/anie.201411854

A metal–organic framework material that functions as an enantioselective catalyst for olefin epoxidation
journal, January 2006

  • Cho, So-Hye; Ma, Baoqing; Nguyen, SonBinh T.
  • Chem. Commun., Vol. 0, Issue 24, p. 2563-2565
  • DOI: 10.1039/B600408C

Structures of Metal–Organic Frameworks with Rod Secondary Building Units
journal, September 2016


Electron delocalization and charge mobility as a function of reduction in a metal–organic framework
journal, June 2018


Reticular Chemistry: Occurrence and Taxonomy of Nets and Grammar for the Design of Frameworks
journal, March 2005

  • Ockwig, Nathan W.; Delgado-Friedrichs, Olaf; O'Keeffe, Michael
  • Accounts of Chemical Research, Vol. 38, Issue 3, p. 176-182
  • DOI: 10.1021/ar020022l

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

  • Nelson, Andrew P.; Farha, Omar K.; Mulfort, Karen L.
  • Journal of the American Chemical Society, Vol. 131, Issue 2, p. 458-460
  • DOI: 10.1021/ja808853q

Porous materials with optimal adsorption thermodynamics and kinetics for CO2 separation
journal, February 2013

  • Nugent, Patrick; Belmabkhout, Youssef; Burd, Stephen D.
  • Nature, Vol. 495, Issue 7439, p. 80-84
  • DOI: 10.1038/nature11893

Inside Cover: A Rotational BODIPY Nucleotide: An Environment-Sensitive Fluorescence-Lifetime Probe for DNA Interactions and Applications in Live-Cell Microscopy (Angew. Chem. Int. Ed. 1/2016)
journal, December 2015

  • Dziuba, Dmytro; Jurkiewicz, Piotr; Cebecauer, Marek
  • Angewandte Chemie International Edition, Vol. 55, Issue 1
  • DOI: 10.1002/anie.201510985

Measuring and Reporting Electrical Conductivity in Metal–Organic Frameworks: Cd 2 (TTFTB) as a Case Study
journal, October 2016

  • Sun, Lei; Park, Sarah S.; Sheberla, Dennis
  • Journal of the American Chemical Society, Vol. 138, Issue 44
  • DOI: 10.1021/jacs.6b09345

Zirconium-Metalloporphyrin PCN-222: Mesoporous Metal-Organic Frameworks with Ultrahigh Stability as Biomimetic Catalysts
journal, August 2012

  • Feng, Dawei; Gu, Zhi-Yuan; Li, Jian-Rong
  • Angewandte Chemie International Edition, Vol. 51, Issue 41
  • DOI: 10.1002/anie.201204475