ACS Publications. Most Trusted. Most Cited. Most Read
Pressure Induced Phase Transitions and Metallization of a Neutral Radical Conductor
My Activity

Figure 1Loading Img
    Article

    Pressure Induced Phase Transitions and Metallization of a Neutral Radical Conductor
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada
    Department of Earth Sciences, University of Western Ontario, London, Ontario N6A 5B7, Canada
    § Department of Physics and Engineering Physics, University of Saskatchewan, Saskatoon, Saskatchewan S7N 5E2, Canada
    # Department of Physics, University of Ottawa, Ottawa, Ontario K1N 6N5, Canada
    Materials Science Division, Japan Synchrotron Radiation Research Institute (JASRI), SPring-8, Sayo, Hyogo 679-5198, Japan
    Canadian Light Source, Saskatoon, Saskatchewan S7N 5B3, Canada
    Other Access OptionsSupporting Information (7)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2014, 136, 3, 1070–1081
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja411057x
    Published January 8, 2014
    Copyright © 2014 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The crystal structure and charge transport properties of the prototypal oxobenzene-bridged 1,2,3-bisdithiazolyl radical conductor 3a are strongly dependent on pressure. Compression of the as-crystallized α-phase, space group Fdd2, to 3–4 GPa leads to its conversion into a second or β-phase, in which F-centering is lost. The space group symmetry is lowered to Pbn21, and there is concomitant halving of the a and b axes. A third or γ-phase, also space group Pbn21, is generated by further compression to 8 GPa. The changes in packing that accompany both phase transitions are associated with an “ironing out” of the ruffled ribbon-like architecture of the α-phase, so that consecutive radicals along the ribbons are rendered more nearly coplanar. In the β-phase the planar ribbons are propagated along the b-glides, while in the γ-phase they follow the n-glides. At ambient pressure 3a is a Mott insulator, displaying high but activated conductivity, with σ(300 K) = 6 × 10–3 S cm–1 and Eact = 0.16 eV. With compression beyond 4 GPa, its conductivity is increased by 3 orders of magnitude, and the thermal activation energy is reduced to zero, heralding the formation of a metallic state. High pressure infrared absorption and reflectivity measurements are consistent with closure of the Mott–Hubbard gap near 4–5 GPa. The results are discussed in the light of DFT calculations on the molecular and band electronic structure of 3a. The presence of a low-lying LUMO in 3a gives rise to high electron affinity which, in turn, creates an electronically much softer radical with a low onsite Coulomb potential U. In addition, considerable crystal orbital (SOMO/LUMO) mixing occurs upon pressurization, so that a metallic state is readily achieved at relatively low applied pressure.

    Copyright © 2014 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Complete refs 57 and 58. Details of high-pressure crystallographic data collection and structure refinement for 3a, and Gaussian 09 archive files. This information is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 72 publications.

    1. Mercè Deumal, Jordi Ribas-Ariño, Cristina Roncero, Michael A. Robb. Real-Time CASSCF (Ehrenfest) Modeling of Electron Dynamics in Organic Semiconductors. Dynamics Reaction Paths Driven by Quantum Coherences. Application to a Radical Organic Semiconductor. The Journal of Physical Chemistry A 2024, 128 (49) , 10555-10567. https://doi.org/10.1021/acs.jpca.4c06466
    2. Shuichi Suzuki, Ryochi Maya, Yoshiaki Uchida, Takeshi Naota. Strategy for Stimuli-Induced Spin Control Using a Liquescent Radical Cation. ACS Omega 2019, 4 (6) , 10031-10035. https://doi.org/10.1021/acsomega.9b00982
    3. Aaron Mailman, Craig M. Robertson, Stephen M. Winter, Paul A. Dube, Richard T. Oakley. The Importance of Electronic Dimensionality in Multiorbital Radical Conductors. Inorganic Chemistry 2019, 58 (9) , 6495-6506. https://doi.org/10.1021/acs.inorgchem.9b00691
    4. Yassine Beldjoudi, Ana Arauzo, Javier Campo, Emma L. Gavey, Melanie Pilkington, Mitchell A. Nascimento, Jeremy M. Rawson. Structural, Magnetic, and Optical Studies of the Polymorphic 9′-Anthracenyl Dithiadiazolyl Radical. Journal of the American Chemical Society 2019, 141 (17) , 6875-6889. https://doi.org/10.1021/jacs.8b11528
    5. Taeyeon Kwon, Jin Young Koo, Hee Cheul Choi. Surface-Mediated Recrystallization for Highly Conducting Organic Radical Crystal. Crystal Growth & Design 2019, 19 (2) , 551-555. https://doi.org/10.1021/acs.cgd.8b01686
    6. Yann Le Gal, Thierry Roisnel, Pascale Auban-Senzier, Nathalie Bellec, Jorge Íñiguez, Enric Canadell, Dominique Lorcy. Stable Metallic State of a Neutral-Radical Single-Component Conductor at Ambient Pressure. Journal of the American Chemical Society 2018, 140 (22) , 6998-7004. https://doi.org/10.1021/jacs.8b03714
    7. Yassine Beldjoudi, Mitchell A. Nascimento, Yong Joo Cho, Hyeonghwa Yu, Hany Aziz, Daiki Tonouchi, Keitaro Eguchi, Michio M. Matsushita, Kunio Awaga, Igor Osorio-Roman, Christos P. Constantinides, Jeremy M. Rawson. Multifunctional Dithiadiazolyl Radicals: Fluorescence, Electroluminescence, and Photoconducting Behavior in Pyren-1′-yl-dithiadiazolyl. Journal of the American Chemical Society 2018, 140 (20) , 6260-6270. https://doi.org/10.1021/jacs.7b12592
    8. Tomokatsu Kushida, Shusuke Shirai, Naoki Ando, Toshihiro Okamoto, Hiroyuki Ishii, Hiroyuki Matsui, Masakazu Yamagishi, Takafumi Uemura, Junto Tsurumi, Shun Watanabe, Jun Takeya, and Shigehiro Yamaguchi . Boron-Stabilized Planar Neutral π-Radicals with Well-Balanced Ambipolar Charge-Transport Properties. Journal of the American Chemical Society 2017, 139 (41) , 14336-14339. https://doi.org/10.1021/jacs.7b05471
    9. Aaron Mailman, Joanne W. L. Wong, Stephen M. Winter, Robert C. M. Claridge, Craig M. Robertson, Abdeljalil Assoud, Wenjun Yong, Eden Steven, Paul A. Dube, John S. Tse, Serge Desgreniers, Richard A. Secco, and Richard T. Oakley . Fine Tuning the Performance of Multiorbital Radical Conductors by Substituent Effects. Journal of the American Chemical Society 2017, 139 (4) , 1625-1635. https://doi.org/10.1021/jacs.6b11779
    10. Manuel Souto, HengBo Cui, Miriam Peña-Álvarez, Valentín G. Baonza, Harald O. Jeschke, Milan Tomic, Roser Valentí, Davide Blasi, Imma Ratera, Concepció Rovira, and Jaume Veciana . Pressure-Induced Conductivity in a Neutral Nonplanar Spin-Localized Radical. Journal of the American Chemical Society 2016, 138 (36) , 11517-11525. https://doi.org/10.1021/jacs.6b02888
    11. Krešimir Molčanov, Vladimir Stilinović, Ana Šantić, Nadica Maltar-Strmečki, Damir Pajić, and Biserka Kojić-Prodić . Fine Tuning of π-Stack Separation Distances of Semiquinone Radicals Affects Their Magnetic and Electric Properties. Crystal Growth & Design 2016, 16 (9) , 4777-4782. https://doi.org/10.1021/acs.cgd.6b00675
    12. Agathe Filatre-Furcate, Nathalie Bellec, Olivier Jeannin, Pascale Auban-Senzier, Marc Fourmigué, Jorge Íñiguez, Enric Canadell, Benjamin Brière, Vinh Ta Phuoc, and Dominique Lorcy . Single-Component Conductors: A Sturdy Electronic Structure Generated by Bulky Substituents. Inorganic Chemistry 2016, 55 (12) , 6036-6046. https://doi.org/10.1021/acs.inorgchem.6b00556
    13. Dawei Zhang and Chungen Liu . Electronic Structures of Anti-Ferromagnetic Tetraradicals: Ab Initio and Semi-Empirical Studies. Journal of Chemical Theory and Computation 2016, 12 (4) , 1714-1727. https://doi.org/10.1021/acs.jctc.6b00103
    14. Di Tian, Stephen M. Winter, Aaron Mailman, Joanne W. L. Wong, Wenjun Yong, Hiroshi Yamaguchi, Yating Jia, John S. Tse, Serge Desgreniers, Richard A. Secco, Stephen R. Julian, Changqing Jin, Masaki Mito, Yasuo Ohishi, and Richard T. Oakley . The Metallic State in Neutral Radical Conductors: Dimensionality, Pressure and Multiple Orbital Effects. Journal of the American Chemical Society 2015, 137 (44) , 14136-14148. https://doi.org/10.1021/jacs.5b08254
    15. Toshiki Higashino, Olivier Jeannin, Tadashi Kawamoto, Dominique Lorcy, Takehiko Mori, and Marc Fourmigué . A Single-Component Conductor Based on a Radical Gold Dithiolene Complex with Alkyl-Substituted Thiophene-2,3-dithiolate Ligand. Inorganic Chemistry 2015, 54 (20) , 9908-9913. https://doi.org/10.1021/acs.inorgchem.5b01678
    16. Pradip Bag, Mikhail E. Itkis, Dejan Stekovic, Sushanta K. Pal, Fook S. Tham, and Robert C. Haddon . Band Structure Engineering by Substitutional Doping in Solid-State Solutions of [5-Me-PLY(O,O)]2B(1–x)Bex Radical Crystals. Journal of the American Chemical Society 2015, 137 (31) , 10000-10008. https://doi.org/10.1021/jacs.5b06145
    17. Nathan J. Yutronkie, Alicea A. Leitch, Ilia Korobkov, and Jaclyn L. Brusso . 1,2,4,6-Thiatriazinyl Radicals and Dimers: Structural and Electronic Tuning through Heteroaromatic Substituent Modification. Crystal Growth & Design 2015, 15 (5) , 2524-2532. https://doi.org/10.1021/acs.cgd.5b00296
    18. Stephen M. Winter, Stephen Hill, and Richard T. Oakley . Magnetic Ordering and Anisotropy in Heavy Atom Radicals. Journal of the American Chemical Society 2015, 137 (11) , 3720-3730. https://doi.org/10.1021/jacs.5b00672
    19. Adam Jaffe, Yu Lin, Wendy L. Mao, and Hemamala I. Karunadasa . Pressure-Induced Conductivity and Yellow-to-Black Piezochromism in a Layered Cu–Cl Hybrid Perovskite. Journal of the American Chemical Society 2015, 137 (4) , 1673-1678. https://doi.org/10.1021/ja512396m
    20. Aaron Mailman, Stephen M. Winter, Joanne W. L. Wong, Craig M. Robertson, Abdeljalil Assoud, Paul A. Dube, and Richard T. Oakley . Multiple Orbital Effects and Magnetic Ordering in a Neutral Radical. Journal of the American Chemical Society 2015, 137 (3) , 1044-1047. https://doi.org/10.1021/ja512235h
    21. Sushanta K. Pal, Pradip Bag, Mikhail E. Itkis, Fook S. Tham, and Robert C. Haddon . Enhanced Electrical Conductivity in a Substitutionally Doped Spiro-bis(phenalenyl)boron Radical Molecular Solid. Journal of the American Chemical Society 2014, 136 (42) , 14738-14741. https://doi.org/10.1021/ja508903z
    22. Christos P. Constantinides, Andrey A. Berezin, Georgia A. Zissimou, Maria Manoli, Gregory M. Leitus, Michael Bendikov, Michael R. Probert, Jeremy M. Rawson, and Panayiotis A. Koutentis . A Magnetostructural Investigation of an Abrupt Spin Transition for 1-Phenyl-3-trifluoromethyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl. Journal of the American Chemical Society 2014, 136 (34) , 11906-11909. https://doi.org/10.1021/ja5063746
    23. P. A. Koutentis, A. Yu. Makarov, O. A. Rakitin, A. V. Zibarev. Herz chemistry and its applications in small-molecule functional materials science: achievements, challenges, and prospects. Russian Chemical Reviews 2025, 94 (1) , RCR5146. https://doi.org/10.59761/RCR5146
    24. C. Roncero-Barrero, M. A. Carvajal, J. Ribas-Ariño, I. de P. R. Moreira, M. Deumal. Understanding trends in conductivity in four isostructural multifunctional crystals of Se substituted bis-dithiazolyl radicals. Journal of Materials Chemistry C 2024, 12 (2) , 468-480. https://doi.org/10.1039/D3TC03710J
    25. Oleg A. Rakitin. Strategies for the annulation of five-membered sulfur-nitrogen rings to benzene and heterocycles. 2024, 227-281. https://doi.org/10.1016/bs.aihch.2023.05.001
    26. Ewa Napiórkowska, Katarzyna Milcarz, Łukasz Szeleszczuk. Review of Applications of Density Functional Theory (DFT) Quantum Mechanical Calculations to Study the High-Pressure Polymorphs of Organic Crystalline Materials. International Journal of Molecular Sciences 2023, 24 (18) , 14155. https://doi.org/10.3390/ijms241814155
    27. Tomofumi Kadoya, Toshiki Higashino. Boundary research between organic conductors and transistors: new trends for functional molecular crystals. CrystEngComm 2023, 25 (27) , 3846-3860. https://doi.org/10.1039/D3CE00305A
    28. Shohei Koyama, Yoji Horii, Tetsu Sato, Shinya Takaishi, Norihisa Hoshino, Tomoyuki Akutagawa, Hiroaki Iguchi. Benzenetriimide‐Based Molecular Conductor with Antiferro‐ to Ferromagnetic Switching Induced by Structural Change of π‐stacked Array. ChemPhysChem 2022, 23 (19) https://doi.org/10.1002/cphc.202200322
    29. C. Roncero-Barrero, J. Ribas-Ariño, I. de P. R. Moreira, M. Deumal. Magnetic coupling and spin ordering in bisdithiazolyl, thiaselenazolyl, and bisdiselenazolyl molecular materials. Dalton Transactions 2022, 51 (34) , 13032-13045. https://doi.org/10.1039/D2DT01340A
    30. Cristina Roncero-Barrero, Jordi Ribas-Ariño, Mercè Deumal, Ibério de P. R. Moreira. Electronic structure and magnetic coupling in selenium substituted pyridine-bridged bisdithiazolyl multifunctional molecular materials. Physical Chemistry Chemical Physics 2022, 24 (20) , 12196-12207. https://doi.org/10.1039/D2CP00415A
    31. Nadia T. Stephaniuk, Mitchell A. Nascimento, Sahar Nikoo, Elodie Heyer, Lara K. Watanabe, Jeremy M. Rawson. Robust S 4 ⋅⋅⋅O Supramolecular Synthons: Structures of Radical‐Radical Cocrystals [ p ‐XC 6 F 4 CNSSN] 2 [TEMPO] (X=F, Cl, Br, I, CN). Chemistry – A European Journal 2022, 28 (15) https://doi.org/10.1002/chem.202103846
    32. Eugeny Viktorovich Tretyakov, Victor Ivanovich Ovcharenko, Alexander Olegovich Terent'ev, Igor Borisovich Krylov, Tatiana Vladimirovna Magdesieva, Dmitrii Gennad'evich Mazhukin, Nina Pavlovna Gritsan. Conjugated nitroxides. Russian Chemical Reviews 2022, 91 (2) https://doi.org/10.1070/RCR5025
    33. Brigitte A. G. Lamers, Martin H. C. van Son, Freek V. de Graaf, Bart W. L. van den Bersselaar, Bas F. M. de Waal, Kazuki Komatsu, Hiroshi Sato, Takuzo Aida, José Augusto Berrocal, Anja R. A. Palmans, Ghislaine Vantomme, Stefan C. J. Meskers, E. W. Meijer. Tuning the donor–acceptor interactions in phase-segregated block molecules. Materials Horizons 2022, 9 (1) , 294-302. https://doi.org/10.1039/D1MH01141C
    34. Claudio D. Navo, Francesca Peccati, Nuria Mazo, Reyes Núñez-Franco, Gonzalo Jiménez-Osés. 1,2-Oxa/Thia-3-Azoles. 2022, 1-55. https://doi.org/10.1016/B978-0-12-818655-8.00115-3
    35. Tsuyoshi Murata, Shogo Matsui, Gunzi Saito. Cytosine-fused TTF: Conducting property of single-component betainic radical and self-assembling ability of hemi-deprotonated cytosine pair. Molecular Crystals and Liquid Crystals 2021, 730 (1) , 23-34. https://doi.org/10.1080/15421406.2021.1946349
    36. Y. Min, G.C. Zhuang, K.L. Yao. Multifunctional molecular spintronics device based on neutral π-radicals predicted by first-principles study. Physics Letters A 2021, 414 , 127633. https://doi.org/10.1016/j.physleta.2021.127633
    37. Sudeshna Samanta, Arun S. Nissimagoudar, Rabaya Basori, Alexei Kuzmin, Mingtao Li, Jinbo Zhang, Lin Wang, Yongjun Tian, Ho-kwang Mao. Unprecedented pressure-driven metallization and topological charge transport in an anion radical salt. Materials Today Physics 2021, 20 , 100467. https://doi.org/10.1016/j.mtphys.2021.100467
    38. Manuel Souto, Dmitrii F. Perepichka. Electrically conductive covalent organic frameworks: bridging the fields of organic metals and 2D materials. Journal of Materials Chemistry C 2021, 9 (33) , 10668-10676. https://doi.org/10.1039/D1TC00750E
    39. Dafei Yuan, Wuyue Liu, Xiaozhang Zhu. Design and Applications of Single-Component Radical Conductors. Chem 2021, 7 (2) , 333-357. https://doi.org/10.1016/j.chempr.2020.10.001
    40. Yuka Kobayashi, Kazuto Hirata, Samantha N. Hood, Hui Yang, Aron Walsh, Yoshitaka Matsushita, Kunie Ishioka. Crystal structure and metallization mechanism of the π-radical metal TED. Chemical Science 2020, 11 (43) , 11699-11704. https://doi.org/10.1039/D0SC03521A
    41. Ryu Tanimoto, Shuichi Suzuki, Masatoshi Kozaki, Yuki Kanzaki, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Rika Tanaka, Keiji Okada. Magnetic Properties of Metal Clusters Coordinated with (Nitronyl Nitroxide)‐Substituted Amidinate Ligands. ChemistrySelect 2020, 5 (36) , 11170-11176. https://doi.org/10.1002/slct.202002927
    42. Tomofumi Kadoya, Shiori Sugiura, Keishiro Tahara, Toshiki Higashino, Kazuya Kubo, Takahiko Sasaki, Kazuo Takimiya, Jun-ichi Yamada. Two-dimensional radical–cationic Mott insulator based on an electron donor containing neither a tetrathiafulvalene nor tetrathiapentalene skeleton. CrystEngComm 2020, 22 (36) , 5949-5953. https://doi.org/10.1039/D0CE00878H
    43. Ryoya Sato, Masaki Matsuda. Formation of Three-Dimensional Electronic Networks Using Axially Ligated Metal Phthalocyanines as Stable Neutral Radicals. Crystals 2020, 10 (9) , 747. https://doi.org/10.3390/cryst10090747
    44. Yulia M. Volkova, Alexander Yu. Makarov, Elena A. Pritchina, Nina P. Gritsan, Andrey V. Zibarev. Herz radicals: chemistry and materials science. Mendeleev Communications 2020, 30 (4) , 385-394. https://doi.org/10.1016/j.mencom.2020.07.001
    45. Atsuki Nagata, Shinsuke Hiraoka, Shuichi Suzuki, Masatoshi Kozaki, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Rika Tanaka, Keiji Okada. Redox‐Induced Modulation of Exchange Interaction in a High‐Spin Ground‐State Diradical/Triradical System. Chemistry – A European Journal 2020, 26 (14) , 3166-3172. https://doi.org/10.1002/chem.201905465
    46. John S Tse. A chemical perspective on high pressure crystal structures and properties. National Science Review 2020, 7 (1) , 149-169. https://doi.org/10.1093/nsr/nwz144
    47. Krešimir Molčanov, Valentina Milašinović, Nives Ivić, Vladimir Stilinović, Dinko Kolarić, Biserka Kojić-Prodić. Influence of organic cations on the stacking of semiquinone radical anions. CrystEngComm 2019, 21 (45) , 6920-6928. https://doi.org/10.1039/C9CE00919A
    48. Dafei Yuan, Dazhen Huang, Samara Medina Rivero, Abel Carreras, Cheng Zhang, Ye Zou, Xuechen Jiao, Christopher R. McNeill, Xiaozhang Zhu, Chong-an Di, Daoben Zhu, David Casanova, Juan Casado. Cholesteric Aggregation at the Quinoidal-to-Diradical Border Enabled Stable n-Doped Conductor. Chem 2019, 5 (4) , 964-976. https://doi.org/10.1016/j.chempr.2019.02.010
    49. Dejan Stekovic, Pradip Bag, Pritam Shankhari, Boniface P. T. Fokwa, Mikhail E. Itkis. Effect of Substitution on the Hysteretic Phase Transition in a Bistable Phenalenyl‐Based Neutral Radical Molecular Conductor. Chemistry – A European Journal 2019, 25 (16) , 4166-4174. https://doi.org/10.1002/chem.201805816
    50. Tsuyoshi Murata, Chiaki Yamada, Ko Furukawa, Yasushi Morita. Mixed valence salts based on carbon-centered neutral radical crystals. Communications Chemistry 2018, 1 (1) https://doi.org/10.1038/s42004-018-0048-5
    51. Manuel Souto, Maria Chiara Gullo, HengBo Cui, Nicola Casati, Fabio Montisci, Harald O. Jeschke, Roser Valentí, Imma Ratera, Concepció Rovira, Jaume Veciana. Role of the Open‐Shell Character on the Pressure‐Induced Conductivity of an Organic Donor–Acceptor Radical Dyad. Chemistry – A European Journal 2018, 24 (21) , 5500-5505. https://doi.org/10.1002/chem.201800881
    52. B. Brière, J. Caillaux, Y. Le Gal, D. Lorcy, S. Lupi, A. Perucchi, M. Zaghrioui, J. C. Soret, R. Sopracase, V. Ta Phuoc. Interplay between bandwidth-controlled and filling-controlled pressure-induced Mott insulator to metal transition in the molecular compound [Au(Et-thiazdt) 2 ] . Physical Review B 2018, 97 (3) https://doi.org/10.1103/PhysRevB.97.035101
    53. Agathe Filatre‐Furcate, Thierry Roisnel, Marc Fourmigué, Olivier Jeannin, Nathalie Bellec, Pascale Auban‐Senzier, Dominique Lorcy. Subtle Steric Differences Impact the Structural and Conducting Properties of Radical Gold Bis(dithiolene) Complexes. Chemistry – A European Journal 2017, 23 (63) , 16004-16013. https://doi.org/10.1002/chem.201703172
    54. Yuka Kobayashi, Takeshi Terauchi, Satoshi Sumi, Yoshitaka Matsushita. Carrier generation and electronic properties of a single-component pure organic metal. Nature Materials 2017, 16 (1) , 109-114. https://doi.org/10.1038/nmat4768
    55. Manuel Souto, Concepció Rovira, Imma Ratera, Jaume Veciana. TTF–PTM dyads: from switched molecular self assembly in solution to radical conductors in solid state. CrystEngComm 2017, 19 (2) , 197-206. https://doi.org/10.1039/C6CE01660J
    56. Krešimir Molčanov, Biserka Kojić-Prodić. Spin pairing, electrostatic and dipolar interactions influence stacking of radical anions in alkali salts of 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (DDQ). CrystEngComm 2017, 19 (13) , 1801-1808. https://doi.org/10.1039/C7CE00261K
    57. Lucie Routaboul, Iori Tanabe, Juan Colon Santana, Minghui Yuan, Alessio Ghisolfi, William Serrano Garcia, Peter A. Dowben, Bernard Doudin, Pierre Braunstein. Changes in molecular film metallicity with minor modifications of the constitutive quinonoid zwitterions. RSC Advances 2017, 7 (35) , 21906-21917. https://doi.org/10.1039/C7RA01597F
    58. Qi Sui, Ye Yuan, Ning-Ning Yang, Xin Li, Teng Gong, En-Qing Gao, Lin Wang. Coordination-modulated piezochromism in metal–viologen materials. Journal of Materials Chemistry C 2017, 5 (47) , 12400-12408. https://doi.org/10.1039/C7TC04208F
    59. Akira Ueda, Junya Yoshida, Kazuyuki Takahashi, Hatsumi Mori. Development of Novel Functional Molecular Crystals by Utilizing Dynamic Hydrogen Bonds. Journal of Synthetic Organic Chemistry, Japan 2017, 75 (10) , 1045-1054. https://doi.org/10.5059/yukigoseikyokaishi.75.1045
    60. Mario Vazdar, Mirjana Eckert‐Maksić, Hans Lischka. The Antiferromagnetic Spin Coupling in Non‐Kekulé Acenes—Impressive Polyradical Character Revealed by High‐Level Multireference Methods. ChemPhysChem 2016, 17 (13) , 2013-2021. https://doi.org/10.1002/cphc.201600103
    61. Shinsuke Nishida, Yasushi Morita. Air‐Stable Redox‐Active Neutral Radicals. 2016, 177-243. https://doi.org/10.1002/9781118858981.ch6
    62. Kristina Lekin, Kazuma Ogata, Adrian Maclean, Aaron Mailman, Stephen M. Winter, Abdeljalil Assoud, Masaki Mito, John S. Tse, Serge Desgreniers, Naohisa Hirao, Paul A. Dube, Richard T. Oakley. Pushing T C to 27.5 K in a heavy atom radical ferromagnet. Chemical Communications 2016, 52 (96) , 13877-13880. https://doi.org/10.1039/C6CC07142B
    63. Maria Fumanal, Mercè Deumal. The quest for rationalizing the magnetism in purely organic semiquinone-bridged bisdithiazolyl molecular magnets. Physical Chemistry Chemical Physics 2016, 18 (30) , 20738-20749. https://doi.org/10.1039/C6CP02699K
    64. Roberto Boto, Miriam Marqués, Armando Beltrán, Lourdes Gracia, Juan Andrés, Vanessa Riffet, Vanessa Labet, Julia Contreras-García. Chemical Bonding under Pressure. 2015, 131-157. https://doi.org/10.1201/b19417-7
    65. Jianbao Zhao, Zhenxian Liu, Robert A. Gordon, Kenichi Takarabe, Joel Reid, John S. Tse. Pressure-induced phase transition and electrical properties of thermoelectric Al-doped Mg2Si. Journal of Applied Physics 2015, 118 (14) https://doi.org/10.1063/1.4933069
    66. Rei Yoshida, Takeshi Kodama, Koichi Kikuchi, Shinobu Aoyagi, Wataru Fujita. Crystal structure and magnetic properties of the charge-transfer complex (BDTA)2(H3O)2[Fe(II)(CN)6]. Synthetic Metals 2015, 208 , 43-48. https://doi.org/10.1016/j.synthmet.2015.05.011
    67. Georges Trinquier, Jean‐Paul Malrieu. Kekulé versus Lewis: When Aromaticity Prevents Electron Pairing and Imposes Polyradical Character. Chemistry – A European Journal 2015, 21 (2) , 814-828. https://doi.org/10.1002/chem.201403952
    68. Jianbao Zhao, Zhenxian Liu, Joel Reid, Kenichi Takarabe, Tsutomu Iida, Bosen Wang, Uwatoko Yoshiya, John S. Tse. Thermoelectric and electrical transport properties of Mg 2 Si multi-doped with Sb, Al and Zn. Journal of Materials Chemistry A 2015, 3 (39) , 19774-19782. https://doi.org/10.1039/C5TA03751D
    69. Hengbo Cui, Takao Tsumuraya, Tsuyoshi Miyazaki, Yoshinori Okano, Reizo Kato. Pressure‐Induced Metallic Conductivity in the Single‐Component Molecular Crystal [Ni(dmit) 2 ]. European Journal of Inorganic Chemistry 2014, 2014 (24) , 3837-3840. https://doi.org/10.1002/ejic.201400130
    70. Stephen M. Winter, Aaron Mailman, Richard T. Oakley, Komalavalli Thirunavukkuarasu, Stephen Hill, David E. Graf, Stanley W. Tozer, John S. Tse, Masaki Mito, Hiroshi Yamaguchi. Electronic and magnetic structure of neutral radical FBBO. Physical Review B 2014, 89 (21) https://doi.org/10.1103/PhysRevB.89.214403
    71. Georges Trinquier, Vijay Gopal Chilkuri, Jean-Paul Malrieu. When a single hole aligns several spins: Double exchange in organic systems. The Journal of Chemical Physics 2014, 140 (20) https://doi.org/10.1063/1.4878498
    72. Alicea A. Leitch, Ilia Korobkov, Abdeljalil Assoud, Jaclyn L. Brusso. Non-innocent pyridyl nitrogens: unprecedented interconversion of N-bridgehead-thiadiazolium salts and thiatriazine in the generation of thiatriazinyl. Chemical Communications 2014, 50 (38) , 4934. https://doi.org/10.1039/c4cc01433b

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2014, 136, 3, 1070–1081
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja411057x
    Published January 8, 2014
    Copyright © 2014 American Chemical Society

    Article Views

    2240

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.