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

Title: Effect of Substitution on the Hysteretic Phase Transition in a Bistable Phenalenyl‐Based Neutral Radical Molecular Conductor

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [4]
  1. Department of ChemistryUniversity of California, Riverside Riverside CA 92521 USA, Center for Nanoscale Science and EngineeringUniversity of California, Riverside Riverside CA 92521 USA
  2. Department of ChemistryUniversity of California, Riverside Riverside CA 92521 USA
  3. Department of ChemistryUniversity of California, Riverside Riverside CA 92521 USA, Department of Chemical and Environmental EngineeringUniversity of California, Riverside Riverside CA 92521 USA
  4. Department of ChemistryUniversity of California, Riverside Riverside CA 92521 USA, Center for Nanoscale Science and EngineeringUniversity of California, Riverside Riverside CA 92521 USA, Department of Chemical and Environmental EngineeringUniversity of California, Riverside Riverside CA 92521 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1494953
Grant/Contract Number:  
FG02-04ER46138
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Name: Chemistry - A European Journal Journal Volume: 25 Journal Issue: 16; Journal ID: ISSN 0947-6539
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Stekovic, Dejan, Bag, Pradip, Shankhari, Pritam, Fokwa, Boniface P. T., and Itkis, Mikhail E. Effect of Substitution on the Hysteretic Phase Transition in a Bistable Phenalenyl‐Based Neutral Radical Molecular Conductor. Germany: N. p., 2019. Web. doi:10.1002/chem.201805816.
Stekovic, Dejan, Bag, Pradip, Shankhari, Pritam, Fokwa, Boniface P. T., & Itkis, Mikhail E. Effect of Substitution on the Hysteretic Phase Transition in a Bistable Phenalenyl‐Based Neutral Radical Molecular Conductor. Germany. doi:10.1002/chem.201805816.
Stekovic, Dejan, Bag, Pradip, Shankhari, Pritam, Fokwa, Boniface P. T., and Itkis, Mikhail E. Mon . "Effect of Substitution on the Hysteretic Phase Transition in a Bistable Phenalenyl‐Based Neutral Radical Molecular Conductor". Germany. doi:10.1002/chem.201805816.
@article{osti_1494953,
title = {Effect of Substitution on the Hysteretic Phase Transition in a Bistable Phenalenyl‐Based Neutral Radical Molecular Conductor},
author = {Stekovic, Dejan and Bag, Pradip and Shankhari, Pritam and Fokwa, Boniface P. T. and Itkis, Mikhail E.},
abstractNote = {},
doi = {10.1002/chem.201805816},
journal = {Chemistry - A European Journal},
number = 16,
volume = 25,
place = {Germany},
year = {2019},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/chem.201805816

Save / Share:

Works referenced in this record:

Chemical strain formation through anion substitution in Cu 2 WS 4 for efficient electrocatalysis of water dissociation
journal, January 2018

  • Tiwari, Anand P.; Azam, Ashraful; Novak, Travis G.
  • Journal of Materials Chemistry A, Vol. 6, Issue 17
  • DOI: 10.1039/C8TA01061G

Crossing the Insulator-to-Metal Barrier with a Thiazyl Radical Conductor
journal, June 2012

  • Mailman, Aaron; Winter, Stephen M.; Yu, Xin
  • Journal of the American Chemical Society, Vol. 134, Issue 24
  • DOI: 10.1021/ja303169y

Resonance Balance Shift in Stacks of Delocalized Singlet Biradicals
journal, July 2009

  • Shimizu, Akihiro; Uruichi, Mikio; Yakushi, Kyuya
  • Angewandte Chemie International Edition, Vol. 48, Issue 30
  • DOI: 10.1002/anie.200901382

Synthesis and Electrical Properties of Tungsten-Doped Vanadium Dioxide Nanopowders by Thermolysis
journal, December 2006

  • Peng, Zifei; Jiang, Wei; Liu, Heng
  • The Journal of Physical Chemistry C, Vol. 111, Issue 3
  • DOI: 10.1021/jp066342u

Effects of Ti–W codoping on the optical and electrical switching of vanadium dioxide thin films grown by a reactive pulsed laser deposition
journal, September 2004

  • Soltani, M.; Chaker, M.; Haddad, E.
  • Applied Physics Letters, Vol. 85, Issue 11
  • DOI: 10.1063/1.1788883

Hetero-π-Dimers of Phenalenyls
journal, November 2015

  • Mou, Zhongyu; Kubo, Takashi; Kertesz, Miklos
  • Chemistry - A European Journal, Vol. 21, Issue 50
  • DOI: 10.1002/chem.201503409

The Metallic State in Neutral Radical Conductors: Dimensionality, Pressure and Multiple Orbital Effects
journal, October 2015

  • Tian, Di; Winter, Stephen M.; Mailman, Aaron
  • Journal of the American Chemical Society, Vol. 137, Issue 44
  • DOI: 10.1021/jacs.5b08254

Unravelling the Key Driving Forces of the Spin Transition in π-Dimers of Spiro-biphenalenyl-Based Radicals
journal, September 2015

  • Fumanal, Maria; Mota, Fernando; Novoa, Juan J.
  • Journal of the American Chemical Society, Vol. 137, Issue 40
  • DOI: 10.1021/jacs.5b04053

Pressure Induced Phase Transitions and Metallization of a Neutral Radical Conductor
journal, January 2014

  • Wong, Joanne W. L.; Mailman, Aaron; Lekin, Kristina
  • Journal of the American Chemical Society, Vol. 136, Issue 3
  • DOI: 10.1021/ja411057x

Synthesis and Characterization of a Highly Reducing Neutral “Extended Viologen” and the Isostructural Hydrocarbon 4,4‘ ‘‘ ‘-Di- n -octyl- p -quaterphenyl
journal, November 2005

  • Porter, William W.; Vaid, Thomas P.; Rheingold, Arnold L.
  • Journal of the American Chemical Society, Vol. 127, Issue 47
  • DOI: 10.1021/ja053084q

Electron delocalization in 9-oxidophenalenone complexes of boron and beryllium
journal, January 1986


Rotational Barrier in Phenalenyl Neutral Radical Dimer: Separating Pancake and van der Waals Interactions
journal, April 2014

  • Cui, Zhong-hua; Lischka, Hans; Beneberu, Habtamu Z.
  • Journal of the American Chemical Society, Vol. 136, Issue 15
  • DOI: 10.1021/ja412862n

Theoretical Analysis of Intermolecular Covalent π−π Bonding and Magnetic Properties of Phenalenyl and spiro -Biphenalenyl Radical π-Dimers
journal, July 2007

  • Huang, Jingsong; Kertesz, Miklos
  • The Journal of Physical Chemistry A, Vol. 111, Issue 28
  • DOI: 10.1021/jp072086p

Bistable Electrical, Optical, and Magnetic Behavior in a Molecule-Based Material
journal, January 2003


Synthesis and characterization of VO2-based thermochromic thin films for energy-efficient windows
journal, April 2011

  • Batista, Carlos; Ribeiro, Ricardo M.; Teixeira, Vasco
  • Nanoscale Research Letters, Vol. 6, Issue 1
  • DOI: 10.1186/1556-276X-6-301

Influence of metal substitution on hybrid halide perovskites: towards lead-free perovskite solar cells
journal, January 2018

  • Chatterjee, Soumyo; Pal, Amlan J.
  • Journal of Materials Chemistry A, Vol. 6, Issue 9
  • DOI: 10.1039/C7TA09943F

Dimerization Transition in Phenalenyl-based Neutral Radicals at High Magnetic Fields
conference, January 2006

  • Jorge, G. A.; Kim, K. H.; Jaime, M.
  • LOW TEMPERATURE PHYSICS: 24th International Conference on Low Temperature Physics - LT24, AIP Conference Proceedings
  • DOI: 10.1063/1.2355191

Origin of Bistability in the Butyl-Substituted Spirobiphenalenyl-Based Neutral Radical Material
journal, May 2017

  • Fumanal, Maria; Novoa, Juan J.; Ribas-Arino, Jordi
  • Chemistry - A European Journal, Vol. 23, Issue 32
  • DOI: 10.1002/chem.201700946

Characterizing the Dimerizations of Phenalenyl Radicals by ab Initio Calculations and Spectroscopy:  σ-Bond Formation versus Resonance π-Stabilization
journal, December 2005

  • Small, David; Rosokha, Sergiy V.; Kochi, Jay K.
  • The Journal of Physical Chemistry A, Vol. 109, Issue 49
  • DOI: 10.1021/jp054244n

Hysteretic Spin and Charge Delocalization in a Phenalenyl-Based Molecular Conductor
journal, December 2010

  • Pal, Sushanta K.; Bag, Pradip; Sarkar, Arindam
  • Journal of the American Chemical Society, Vol. 132, Issue 48
  • DOI: 10.1021/ja107201d

Band Structure Engineering by Substitutional Doping in Solid-State Solutions of [5-Me-PLY(O,O)] 2 B (1– x ) Be x Radical Crystals
journal, July 2015

  • Bag, Pradip; Itkis, Mikhail E.; Stekovic, Dejan
  • Journal of the American Chemical Society, Vol. 137, Issue 31
  • DOI: 10.1021/jacs.5b06145

Tungsten and fluorine co-doping of VO2 films
journal, January 2002


The First Phenalenyl-Based Neutral Radical Molecular Conductor
journal, November 1999

  • Chi, X.; Itkis, M. E.; Patrick, B. O.
  • Journal of the American Chemical Society, Vol. 121, Issue 44
  • DOI: 10.1021/ja992040c

Aromaticity and π-bond covalency: prominent intermolecular covalent bonding interaction of a Kekulé hydrocarbon with very significant singlet biradical character
journal, January 2012

  • Shimizu, Akihiro; Hirao, Yasukazu; Matsumoto, Kouzou
  • Chemical Communications, Vol. 48, Issue 45
  • DOI: 10.1039/c2cc31955a

A Single-Component Molecular Superconductor
journal, May 2014

  • Cui, HengBo; Kobayashi, Hayao; Ishibashi, Shoji
  • Journal of the American Chemical Society, Vol. 136, Issue 21
  • DOI: 10.1021/ja503690m

Magnetic Tuning of All-Organic Binary Alloys between Two Stable Radicals
journal, February 2012

  • Seber, Gonca; Freitas, Rafael S.; Mague, Joel T.
  • Journal of the American Chemical Society, Vol. 134, Issue 8
  • DOI: 10.1021/ja2104697

Unexpected Synergy between Magnetic Iron Chains and Stacked B 6 Rings in Nb 6 Fe 1− x Ir 6+ x B 8
journal, August 2014

  • Mbarki, Mohammed; St. Touzani, Rachid; Fokwa, Boniface P. T.
  • Angewandte Chemie, Vol. 126, Issue 48
  • DOI: 10.1002/ange.201406397

Preparation and Characterization of a Neutral π-Radical Molecular Conductor
journal, February 1999

  • Barclay, T. M.; Cordes, A. W.; Haddon, R. C.
  • Journal of the American Chemical Society, Vol. 121, Issue 5
  • DOI: 10.1021/ja983490s

Design of organic metals and superconductors
journal, July 1975


Resonance Balance Shift in Stacks of Delocalized Singlet Biradicals
journal, July 2009

  • Shimizu, Akihiro; Uruichi, Mikio; Yakushi, Kyuya
  • Angewandte Chemie, Vol. 121, Issue 30
  • DOI: 10.1002/ange.200901382

Synthetic organic spin chemistry for structurally well-defined open-shell graphene fragments
journal, February 2011

  • Morita, Yasushi; Suzuki, Shuichi; Sato, Kazunobu
  • Nature Chemistry, Vol. 3, Issue 3
  • DOI: 10.1038/nchem.985

Semiquinone-Bridged Bisdithiazolyl Radicals as Neutral Radical Conductors
journal, January 2012

  • Yu, Xin; Mailman, Aaron; Lekin, Kristina
  • Journal of the American Chemical Society, Vol. 134, Issue 4
  • DOI: 10.1021/ja209841z

Enhanced Electrical Conductivity in a Substitutionally Doped Spiro-bis(phenalenyl)boron Radical Molecular Solid
journal, October 2014

  • Pal, Sushanta K.; Bag, Pradip; Itkis, Mikhail E.
  • Journal of the American Chemical Society, Vol. 136, Issue 42
  • DOI: 10.1021/ja508903z

Bistabiles elektrisches, optisches und magnetisches Verhalten eines molekularen Materials
journal, January 2003


Recent progress in the phase-transition mechanism and modulation of vanadium dioxide materials
journal, July 2018


What's new in stable radical chemistry?
journal, January 2006

  • Hicks, Robin G.
  • Organic & Biomolecular Chemistry, Vol. 5, Issue 9
  • DOI: 10.1039/b617142g

Thermochromism in an organic crystal based on the coexistence of σ- and π-dimers
journal, December 2007

  • Morita, Yasushi; Suzuki, Shuichi; Fukui, Kozo
  • Nature Materials, Vol. 7, Issue 1
  • DOI: 10.1038/nmat2067

Bistable Multifunctionality and Switchable Strong Ferromagnetic-to-Antiferromagnetic Coupling in a One-Dimensional Rhodium(I)–Semiquinonato Complex
journal, May 2014

  • Mitsumi, Minoru; Nishitani, Takashi; Yamasaki, Shota
  • Journal of the American Chemical Society, Vol. 136, Issue 19
  • DOI: 10.1021/ja5017014

Switching Closed-Shell to Open-Shell Phenalenyl: Toward Designing Electroactive Materials
journal, May 2015

  • Pariyar, Anand; Vijaykumar, Gonela; Bhunia, Mrinal
  • Journal of the American Chemical Society, Vol. 137, Issue 18
  • DOI: 10.1021/jacs.5b00272

Unexpected Synergy between Magnetic Iron Chains and Stacked B 6 Rings in Nb 6 Fe 1− x Ir 6+ x B 8
journal, August 2014

  • Mbarki, Mohammed; St. Touzani, Rachid; Fokwa, Boniface P. T.
  • Angewandte Chemie International Edition, Vol. 53, Issue 48
  • DOI: 10.1002/anie.201406397

Hysteretic Spin Crossover between a Bisdithiazolyl Radical and Its Hypervalent σ-Dimer
journal, November 2010

  • Lekin, Kristina; Winter, Stephen M.; Downie, Laura E.
  • Journal of the American Chemical Society, Vol. 132, Issue 45
  • DOI: 10.1021/ja106768z

Bistability and the Phase Transition in 1,3,2-Dithiazolo[4,5- b ]pyrazin-2-yl
journal, November 2004

  • Brusso, Jaclyn L.; Clements, Owen P.; Haddon, Robert C.
  • Journal of the American Chemical Society, Vol. 126, Issue 45
  • DOI: 10.1021/ja044979q

Advances in thermochromic vanadium dioxide films
journal, January 2014

  • Warwick, Michael E. A.; Binions, Russell
  • J. Mater. Chem. A, Vol. 2, Issue 10
  • DOI: 10.1039/C3TA14124A

Stable Delocalized Singlet Biradical Hydrocarbon for Organic Field-Effect Transistors
journal, December 2015

  • Koike, Harunobu; Chikamatsu, Masayuki; Azumi, Reiko
  • Advanced Functional Materials, Vol. 26, Issue 2
  • DOI: 10.1002/adfm.201503650

Dimeric Phenalenyl-Based Neutral Radical Molecular Conductors
journal, May 2001

  • Chi, X.; Itkis, M. E.; Kirschbaum, K.
  • Journal of the American Chemical Society, Vol. 123, Issue 17
  • DOI: 10.1021/ja0039785

Exploring Closed-Shell Cationic Phenalenyl: From Catalysis to Spin Electronics
journal, June 2017

  • Mukherjee, Arup; Sau, Samaresh Chandra; Mandal, Swadhin K.
  • Accounts of Chemical Research, Vol. 50, Issue 7
  • DOI: 10.1021/acs.accounts.7b00141

Synthesis and Substitution Chemistry of Redox-Active Manganese/Cobalt Oxide Nanosheets
journal, February 2018


Intelligent Window Coatings:  Atmospheric Pressure Chemical Vapor Deposition of Tungsten-Doped Vanadium Dioxide
journal, February 2004

  • Manning, Troy D.; Parkin, Ivan P.; Pemble, Martyn E.
  • Chemistry of Materials, Vol. 16, Issue 4
  • DOI: 10.1021/cm034905y

Three-way switching in a cyanide-bridged [CoFe] chain
journal, September 2012

  • Hoshino, Norihisa; Iijima, Fumichika; Newton, Graham N.
  • Nature Chemistry, Vol. 4, Issue 11
  • DOI: 10.1038/nchem.1455

Molybdenum substitutional doping and its effects on phase transition properties in single crystalline vanadium dioxide thin film
journal, November 1999

  • Wu, Z. P.; Miyashita, A.; Yamamoto, S.
  • Journal of Applied Physics, Vol. 86, Issue 9
  • DOI: 10.1063/1.371519

Pancake π–π Bonding Goes Double: Unexpected 4e/All-Sites Bonding in Boron- and Nitrogen-Doped Phenalenyls
journal, June 2015

  • Tian, Yong-Hui; Sumpter, Bobby G.; Du, Shiyu
  • The Journal of Physical Chemistry Letters, Vol. 6, Issue 12
  • DOI: 10.1021/acs.jpclett.5b00857

Phase transition and IR properties of tungsten-doped vanadium dioxide nanopowders
journal, July 2009


Room-Temperature Magnetic Bistability in Organic Radical Crystals
journal, October 1999


A new spin on bistability
journal, February 2011


Effect of Si substitution on the structural and transport properties of superionic Li-argyrodites
journal, January 2018

  • Minafra, Nicolò; Culver, Sean P.; Krauskopf, Thorben
  • Journal of Materials Chemistry A, Vol. 6, Issue 2
  • DOI: 10.1039/C7TA08581H

Resonance-Stabilized 1,2,3-Dithiazolo-1,2,3-dithiazolyls as Neutral π-Radical Conductors
journal, August 2002

  • Beer, Leanne; Brusso, Jaclyn L.; Cordes, A. Wallace
  • Journal of the American Chemical Society, Vol. 124, Issue 32
  • DOI: 10.1021/ja026118s

Magnetic Bistability in a Discrete Organic Radical
journal, August 2016

  • Li, Tao; Tan, Gengwen; Shao, Dong
  • Journal of the American Chemical Society, Vol. 138, Issue 32
  • DOI: 10.1021/jacs.6b05863

Recent Progress in Quinoidal Singlet Biradical Molecules
journal, February 2015


One-Dimensional Metallic Conducting Pathway of Cyclohexyl-Substituted Spiro-Biphenalenyl Neutral Radical Molecular Crystal
journal, February 2006

  • Huang, Jingsong; Kertesz, Miklos
  • Journal of the American Chemical Society, Vol. 128, Issue 5
  • DOI: 10.1021/ja057198d

Optimizing thermochromic VO 2 by co-doping with W and Sr for smart window applications
journal, April 2017

  • Dietrich, Marc K.; Kuhl, Florian; Polity, Angelika
  • Applied Physics Letters, Vol. 110, Issue 14
  • DOI: 10.1063/1.4979700

A theoretical study of electronic structures and intermolecular magnetic interactions for spiro-biphenalenyls
journal, November 2005


Spin crossover with thermal hysteresis: practicalities and lessons learnt
journal, January 2015


Double Pancake Bonds: Pushing the Limits of Strong π–π Stacking Interactions
journal, September 2014

  • Cui, Zhong-hua; Lischka, Hans; Beneberu, Habtamu Z.
  • Journal of the American Chemical Society, Vol. 136, Issue 37
  • DOI: 10.1021/ja505624y

Effect of Cu substitution on the magnetic and electrical properties of Ni–Zn ferrite synthesised by soft chemical method
journal, April 1999


Synthesis, structure and solid state properties of benzannulated phenalenyl based neutral radical conductor: BENZANNULATED PHENALENYL BASED NEUTRAL RADICAL CONDUCTOR
journal, February 2012

  • Bag, Pradip; Itkis, Mikhail E.; Pal, Sushanta K.
  • Journal of Physical Organic Chemistry, Vol. 25, Issue 7
  • DOI: 10.1002/poc.2906

Phenalenyl-Based Open-Shell Polycyclic Aromatic Hydrocarbons
journal, October 2014


Significant changes in phase-transition hysteresis for Ti-doped VO2 films prepared by polymer-assisted deposition
journal, February 2011


Doping of an organic molecular semiconductor by substitutional cocrystallization with a molecular n-dopant
journal, January 2007

  • Porter, William W.; Vaid, Thomas P.
  • J. Mater. Chem., Vol. 17, Issue 5
  • DOI: 10.1039/B610806G

Fine Tuning the Performance of Multiorbital Radical Conductors by Substituent Effects
journal, January 2017

  • Mailman, Aaron; Wong, Joanne W. L.; Winter, Stephen M.
  • Journal of the American Chemical Society, Vol. 139, Issue 4
  • DOI: 10.1021/jacs.6b11779

Magneto-Opto-Electronic Bistability in a Phenalenyl-Based Neutral Radical
journal, May 2002


Design and Synthesis of New Stable Fluorenyl-Based Radicals
journal, August 2014

  • Tian, Yi; Uchida, Kazuyuki; Kurata, Hiroyuki
  • Journal of the American Chemical Society, Vol. 136, Issue 36
  • DOI: 10.1021/ja507005c