ACS Publications. Most Trusted. Most Cited. Most Read
Synthesis and Characterization of Teranthene: A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekulé Structures
My Activity

Figure 1Loading Img
    Communication

    Synthesis and Characterization of Teranthene: A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekulé Structures
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan, Laboratoire de Chimie Théorique, Facultés Universitaires Notre-Dame de la Paix (FUNDP), rue de Bruxelles, 61, B-5000 Namur, Belgium, and Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan
    †Department of Chemistry, Osaka University.
    ‡Department of Materials Engineering Science, Osaka University.
    §Facultés Universitaires Notre-Dame de la Paix (FUNDP).
    ∥Osaka City University.
    Other Access OptionsSupporting Information (2)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2010, 132, 32, 11021–11023
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja1049737
    Published July 26, 2010
    Copyright © 2010 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A teranthene derivative has been successfully isolated in a crystalline form for the first time. Geometrical considerations and physical property investigations indicate that the molecule possesses prominent biradical character in the ground state.

    Copyright © 2010 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!

    Experimental procedures for all new compounds, crystal data, a magnetic susceptibility plot, a crystal packing diagram, details of the theoretical calculations, and a CIF file for 2a. This material 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!

    This article is cited by 291 publications.

    1. Ya Zou, Liuying Jiao, Yi Han, Longbin Ren, Qifeng Zhou, Jishan Wu. Peri-pentacene and Peri-hexacene Diradicaloids. Journal of the American Chemical Society 2024, 146 (40) , 27293-27298. https://doi.org/10.1021/jacs.4c10494
    2. Efrain Vidal, Jr., Lev N. Zakharov, Carlos J. Gómez-García, Michael M. Haley. Probing the Influence of Alkyne Substitution on the Electronic and Magnetic Properties of Diindeno[1,2-b;1′,2′-i]anthracenes. The Journal of Organic Chemistry 2024, 89 (19) , 14515-14519. https://doi.org/10.1021/acs.joc.4c01500
    3. Peipei Liu, Meng-Xiang Wu, Meng-Ling Yu, Hao Kang, Bin Huang, Hai-Bo Yang, Xiao-Li Zhao, Xueliang Shi. Synthesis of Polycyclic Aromatic Compounds by Electrocyclization–Dehydrogenation of Diradicaloids. Organic Letters 2024, 26 (37) , 7914-7919. https://doi.org/10.1021/acs.orglett.4c02886
    4. Takeru Yamada, Daiki Shimizu, Kenji Matsuda. Oxidation of Weakly Interacting Diradicals: An Approach for Strong and Tunable Near-Infrared-Absorbing Dyes Based on Small Chromophores. The Journal of Physical Chemistry Letters 2024, 15 (36) , 9175-9182. https://doi.org/10.1021/acs.jpclett.4c02212
    5. Chaowei Hu, Leah Kuhn, Favour D. Makurvet, Erica S. Knorr, Xinsong Lin, Rahul K. Kawade, Frederic Mentink-Vigier, Kenneth Hanson, Igor V. Alabugin. Tethering Three Radical Cascades for Controlled Termination of Radical Alkyne peri-Annulations: Making Phenalenyl Ketones without Oxidants. Journal of the American Chemical Society 2024, 146 (6) , 4187-4211. https://doi.org/10.1021/jacs.3c13371
    6. Ming-Wei Wang, Wei Fan, Xiaonan Li, Yujian Liu, Zuoyu Li, Wei Jiang, Jishan Wu, Zhaohui Wang. Molecular Carbons: How Far Can We Go?. ACS Nano 2023, 17 (21) , 20734-20752. https://doi.org/10.1021/acsnano.3c07970
    7. Xiushang Xu, Satoshi Takebayashi, Hiroki Hanayama, Serhii Vasylevskyi, Takatsugu Onishi, Tatsuhiko Ohto, Hirokazu Tada, Akimitsu Narita. 6,6′-Biindeno[1,2-b]anthracene: An Open-Shell Biaryl with High Diradical Character. Journal of the American Chemical Society 2023, 145 (7) , 3891-3896. https://doi.org/10.1021/jacs.2c13890
    8. Yuki Hayashi, Shuichi Suzuki, Takanori Suzuki, Yusuke Ishigaki. Dibenzotropylium-Capped Orthogonal Geometry Enabling Isolation and Examination of a Series of Hydrocarbons with Multiple 14π-Aromatic Units. Journal of the American Chemical Society 2023, 145 (4) , 2596-2608. https://doi.org/10.1021/jacs.2c12574
    9. Febin Kuriakose, Michael Commodore, Chaowei Hu, Catherine J. Fabiano, Debashis Sen, Run R. Li, Shubham Bisht, Ökten Üngör, Xinsong Lin, Geoffrey F. Strouse, A. Eugene DePrince, III, Robert A. Lazenby, Frederic Mentink-Vigier, Michael Shatruk, Igor V. Alabugin. Design and Synthesis of Kekulè and Non-Kekulè Diradicaloids via the Radical Periannulation Strategy: The Power of Seven Clar’s Sextets. Journal of the American Chemical Society 2022, 144 (51) , 23448-23464. https://doi.org/10.1021/jacs.2c09637
    10. Tomohiko Nishiuchi, Seito Aibara, Hiroyasu Sato, Takashi Kubo. Synthesis of π-Extended Thiele’s and Chichibabin’s Hydrocarbons and Effect of the π-Congestion on Conformations and Electronic States. Journal of the American Chemical Society 2022, 144 (16) , 7479-7488. https://doi.org/10.1021/jacs.2c02318
    11. Alexander N. Selikhov, Anton V. Cherkasov, Konstantin A. Lyssenko, Alexander A. Trifonov. Thermally Stable Cationic Bis(benzhydryl) Complexes of Early Lanthanides (La, Ce, Nd). Organometallics 2022, 41 (6) , 820-828. https://doi.org/10.1021/acs.organomet.2c00045
    12. Tao Wang, Sofia Sanz, Jesús Castro-Esteban, James Lawrence, Alejandro Berdonces-Layunta, Mohammed S. G. Mohammed, Manuel Vilas-Varela, Martina Corso, Diego Peña, Thomas Frederiksen, Dimas G. de Oteyza. Magnetic Interactions Between Radical Pairs in Chiral Graphene Nanoribbons. Nano Letters 2022, 22 (1) , 164-171. https://doi.org/10.1021/acs.nanolett.1c03578
    13. Shinobu Arikawa, Akihiro Shimizu, Daisuke Shiomi, Kazunobu Sato, Ryo Shintani. Synthesis and Isolation of a Kinetically Stabilized Crystalline Triangulene. Journal of the American Chemical Society 2021, 143 (46) , 19599-19605. https://doi.org/10.1021/jacs.1c10151
    14. Jiaxiang Guo, Yue Yang, Chuandong Dou, Yue Wang. Boron-Containing Organic Diradicaloids: Dynamically Modulating Singlet Diradical Character by Lewis Acid–Base Coordination. Journal of the American Chemical Society 2021, 143 (43) , 18272-18279. https://doi.org/10.1021/jacs.1c08486
    15. James Lawrence, Mohammed S. G. Mohammed, Dulce Rey, Fernando Aguilar-Galindo, Alejandro Berdonces-Layunta, Diego Peña, Dimas G. de Oteyza. Reassessing Alkyne Coupling Reactions While Studying the Electronic Properties of Diverse Pyrene Linkages at Surfaces. ACS Nano 2021, 15 (3) , 4937-4946. https://doi.org/10.1021/acsnano.0c09756
    16. Akihiro Shimizu, Yu Ishizaki, Shun Horiuchi, Takashi Hirose, Kenji Matsuda, Hiroyasu Sato, Jun-ichi Yoshida. HOMO–LUMO Energy-Gap Tuning of π-Conjugated Zwitterions Composed of Electron-Donating Anion and Electron-Accepting Cation. The Journal of Organic Chemistry 2021, 86 (1) , 770-781. https://doi.org/10.1021/acs.joc.0c02343
    17. Yong Ni, Fernando Gordillo-Gámez, Miriam Peña Alvarez, Zhihan Nan, Zhengtao Li, Shaofei Wu, Yi Han, Juan Casado, Jishan Wu. A Chichibabin’s Hydrocarbon-Based Molecular Cage: The Impact of Structural Rigidity on Dynamics, Stability, and Electronic Properties. Journal of the American Chemical Society 2020, 142 (29) , 12730-12742. https://doi.org/10.1021/jacs.0c04876
    18. Kang Cai, Haochuan Mao, Wei-Guang Liu, Yunyan Qiu, Yi Shi, Long Zhang, Dengke Shen, Hongliang Chen, Yang Jiao, Huang Wu, Zhichang Liu, Yuanning Feng, Charlotte L. Stern, Michael R. Wasielewski, William A. Goddard III, J. Fraser Stoddart. Highly Stable Organic Bisradicals Protected by Mechanical Bonds. Journal of the American Chemical Society 2020, 142 (15) , 7190-7197. https://doi.org/10.1021/jacs.0c01989
    19. Shantanu Mishra, Doreen Beyer, Reinhard Berger, Junzhi Liu, Oliver Gröning, José I. Urgel, Klaus Müllen, Pascal Ruffieux, Xinliang Feng, Roman Fasel. Topological Defect-Induced Magnetism in a Nanographene. Journal of the American Chemical Society 2020, 142 (3) , 1147-1152. https://doi.org/10.1021/jacs.9b09212
    20. Jason Melidonie, Evgenia Dmitrieva, Ke Zhang, Yubin Fu, Alexey A. Popov, Wojciech Pisula, Reinhard Berger, Junzhi Liu, Xinliang Feng. Dipyrene-Fused Dicyclopenta[a,f]naphthalenes. The Journal of Organic Chemistry 2020, 85 (1) , 215-223. https://doi.org/10.1021/acs.joc.9b02626
    21. Qiang Chen, Dieter Schollmeyer, Klaus Müllen, Akimitsu Narita. Synthesis of Circumpyrene by Alkyne Benzannulation of Brominated Dibenzo[hi,st]ovalene. Journal of the American Chemical Society 2019, 141 (51) , 19994-19999. https://doi.org/10.1021/jacs.9b10957
    22. Qiang Chen, Stefan Thoms, Sven Stöttinger, Dieter Schollmeyer, Klaus Müllen, Akimitsu Narita, Thomas Basché. Dibenzo[hi,st]ovalene as Highly Luminescent Nanographene: Efficient Synthesis via Photochemical Cyclodehydroiodination, Optoelectronic Properties, and Single-Molecule Spectroscopy. Journal of the American Chemical Society 2019, 141 (41) , 16439-16449. https://doi.org/10.1021/jacs.9b08320
    23. Marc de Wergifosse, Christoph Bannwarth, Stefan Grimme. A Simplified Spin-Flip Time-Dependent Density Functional Theory Approach for the Electronic Excitation Spectra of Very Large Diradicals. The Journal of Physical Chemistry A 2019, 123 (27) , 5815-5825. https://doi.org/10.1021/acs.jpca.9b03176
    24. Akihito Konishi, Koki Horii, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Makoto Yasuda. Open-Shell and Antiaromatic Character Induced by the Highly Symmetric Geometry of the Planar Heptalene Structure: Synthesis and Characterization of a Nonalternant Isomer of Bisanthene. Journal of the American Chemical Society 2019, 141 (26) , 10165-10170. https://doi.org/10.1021/jacs.9b04080
    25. Tanguy Jousselin-Oba, Masashi Mamada, Jérôme Marrot, Antoine Maignan, Chihaya Adachi, Abderrahim Yassar, Michel Frigoli. Excellent Semiconductors Based on Tetracenotetracene and Pentacenopentacene: From Stable Closed-Shell to Singlet Open-Shell. Journal of the American Chemical Society 2019, 141 (23) , 9373-9381. https://doi.org/10.1021/jacs.9b03488
    26. Alexander N. Selikhov, Gleb S. Plankin, Anton V. Cherkasov, Andrey S. Shavyrin, Elisa Louyriac, Laurent Maron, Alexander A. Trifonov. Thermally Stable Ln(II) and Ca(II) Bis(benzhydryl) Complexes: Excellent Precatalysts for Intermolecular Hydrophosphination of C–C Multiple Bonds. Inorganic Chemistry 2019, 58 (8) , 5325-5334. https://doi.org/10.1021/acs.inorgchem.9b00490
    27. Hiroyuki Watanabe, Kazuo Tanaka, Yoshiki Chujo. Independently Tuned Frontier Orbital Energy Levels of 1,3,4,6,9b-Pentaazaphenalene Derivatives by the Conjugation Effect. The Journal of Organic Chemistry 2019, 84 (5) , 2768-2778. https://doi.org/10.1021/acs.joc.8b03161
    28. Caleb M. Wehrmann, Ryan T. Charlton, Mark S. Chen. A Concise Synthetic Strategy for Accessing Ambient Stable Bisphenalenyls toward Achieving Electroactive Open-Shell π-Conjugated Materials. Journal of the American Chemical Society 2019, 141 (7) , 3240-3248. https://doi.org/10.1021/jacs.8b13300
    29. Wangdong Zeng, Tullimilli Y. Gopalakrishna, Hoa Phan, Takayuki Tanaka, Tun Seng Herng, Jun Ding, Atsuhiro Osuka, Jishan Wu. Superoctazethrene: An Open-Shell Graphene-like Molecule Possessing Large Diradical Character but Still with Reasonable Stability. Journal of the American Chemical Society 2018, 140 (43) , 14054-14058. https://doi.org/10.1021/jacs.8b09075
    30. Xuefeng Lu, Sangsu Lee, Yongseok Hong, Hoa Phan, Tullimilli Y. Gopalakrishna, Tun Seng Herng, Takayuki Tanaka, María Eugenia Sandoval-Salinas, Wangdong Zeng, Jun Ding, David Casanova, Atsuhiro Osuka, Dongho Kim, and Jishan Wu . Fluorenyl Based Macrocyclic Polyradicaloids. Journal of the American Chemical Society 2017, 139 (37) , 13173-13183. https://doi.org/10.1021/jacs.7b07335
    31. Suman Ray, Shikha Sharma, Ulrike Salzner, and Satish Patil . Synthesis and Characterization of Quinoidal Diketopyrrolopyrrole Derivatives with Exceptionally High Electron Affinities. The Journal of Physical Chemistry C 2017, 121 (30) , 16088-16097. https://doi.org/10.1021/acs.jpcc.7b04085
    32. Valentin M. Hertz, Naoki Ando, Masato Hirai, Michael Bolte, Hans-Wolfram Lerner, Shigehiro Yamaguchi, and Matthias Wagner . Steric Shielding vs Structural Constraint in a Boron-Containing Polycyclic Aromatic Hydrocarbon. Organometallics 2017, 36 (14) , 2512-2519. https://doi.org/10.1021/acs.organomet.6b00800
    33. Toru Saito, Yasutaka Kitagawa, and Yu Takano . Reparameterization of PM6 Applied to Organic Diradical Molecules. The Journal of Physical Chemistry A 2016, 120 (43) , 8750-8760. https://doi.org/10.1021/acs.jpca.6b08530
    34. Xuefeng Lu, Sangsu Lee, Jun Oh Kim, Tullimilli Y. Gopalakrishna, Hoa Phan, Tun Seng Herng, Zhenglong Lim, Zebing Zeng, Jun Ding, Dongho Kim, and Jishan Wu . Stable 3,6-Linked Fluorenyl Radical Oligomers with Intramolecular Antiferromagnetic Coupling and Polyradical Characters. Journal of the American Chemical Society 2016, 138 (39) , 13048-13058. https://doi.org/10.1021/jacs.6b08138
    35. Rui Huang, Hoa Phan, Tun Seng Herng, Pan Hu, Wangdong Zeng, Shao-qiang Dong, Soumyajit Das, Yongjia Shen, Jun Ding, David Casanova, and Jishan Wu . Higher Order π-Conjugated Polycyclic Hydrocarbons with Open-Shell Singlet Ground State: Nonazethrene versus Nonacene. Journal of the American Chemical Society 2016, 138 (32) , 10323-10330. https://doi.org/10.1021/jacs.6b06188
    36. Jia-Jun Wang, Zhong-Jun Zhou, Hui-Min He, Di Wu, Ying Li, Zhi-Ru Li, and Hong-Xing Zhang . An External Electric Field Manipulated Second-Order Nonlinear Optical Switch of an Electride Molecule: A Long-Range Electron Transfer Forms a Lone Excess Electron Pair and Quenches Singlet Diradical. The Journal of Physical Chemistry C 2016, 120 (25) , 13656-13666. https://doi.org/10.1021/acs.jpcc.6b00745
    37. Soumyajit Das, Tun Seng Herng, José L. Zafra, Paula Mayorga Burrezo, Masaaki Kitano, Masatoshi Ishida, Tullimilli Y. Gopalakrishna, Pan Hu, Atsuhiro Osuka, Juan Casado, Jun Ding, David Casanova, and Jishan Wu . Fully Fused Quinoidal/Aromatic Carbazole Macrocycles with Poly-radical Characters. Journal of the American Chemical Society 2016, 138 (24) , 7782-7790. https://doi.org/10.1021/jacs.6b04539
    38. Priya Yadav, Soumyajit Das, Hoa Phan, Tun Seng Herng, Jun Ding, and Jishan Wu . Kinetically Blocked Stable 5,6:12,13-Dibenzozethrene: A Laterally π-Extended Zethrene with Enhanced Diradical Character. Organic Letters 2016, 18 (12) , 2886-2889. https://doi.org/10.1021/acs.orglett.6b01196
    39. Tim Dumslaff, Bo Yang, Ali Maghsoumi, Gangamallaiah Velpula, Kunal S. Mali, Chiara Castiglioni, Steven De Feyter, Matteo Tommasini, Akimitsu Narita, Xinliang Feng, and Klaus Müllen . Adding Four Extra K-Regions to Hexa-peri-hexabenzocoronene. Journal of the American Chemical Society 2016, 138 (14) , 4726-4729. https://doi.org/10.1021/jacs.6b01976
    40. Pan Hu, Sangsu Lee, Kyu Hyung Park, Soumyajit Das, Tun Seng Herng, Théo P. Gonçalves, Kuo-Wei Huang, Jun Ding, Dongho Kim, and Jishan Wu . Octazethrene and Its Isomer with Different Diradical Characters and Chemical Reactivity: The Role of the Bridge Structure. The Journal of Organic Chemistry 2016, 81 (7) , 2911-2919. https://doi.org/10.1021/acs.joc.6b00172
    41. Patrick E. Hartnett, Eric A. Margulies, Catherine M. Mauck, Stephen A. Miller, Yilei Wu, Yi-Lin Wu, Tobin J. Marks, and Michael R. Wasielewski . Effects of Crystal Morphology on Singlet Exciton Fission in Diketopyrrolopyrrole Thin Films. The Journal of Physical Chemistry B 2016, 120 (7) , 1357-1366. https://doi.org/10.1021/acs.jpcb.5b10565
    42. Kazuyuki Uchida, Soichi Ito, Masayoshi Nakano, Manabu Abe, and Takashi Kubo . Biphenalenylidene: Isolation and Characterization of the Reactive Intermediate on the Decomposition Pathway of Phenalenyl Radical. Journal of the American Chemical Society 2016, 138 (7) , 2399-2410. https://doi.org/10.1021/jacs.5b13033
    43. Pan Hu, Sangsu Lee, Tun Seng Herng, Naoki Aratani, Théo P. Gonçalves, Qingbiao Qi, Xueliang Shi, Hiroko Yamada, Kuo-Wei Huang, Jun Ding, Dongho Kim, and Jishan Wu . Toward Tetraradicaloid: The Effect of Fusion Mode on Radical Character and Chemical Reactivity. Journal of the American Chemical Society 2016, 138 (3) , 1065-1077. https://doi.org/10.1021/jacs.5b12532
    44. Masayoshi Nakano and Benoît Champagne . Theoretical Design of Open-Shell Singlet Molecular Systems for Nonlinear Optics. The Journal of Physical Chemistry Letters 2015, 6 (16) , 3236-3256. https://doi.org/10.1021/acs.jpclett.5b00956
    45. Carlos-Andres Palma, Manohar Awasthi, Yenny Hernandez, Xinliang Feng, Klaus Müllen, Thomas A. Niehaus, and Johannes V. Barth . Sub-Nanometer Width Armchair Graphene Nanoribbon Energy Gap Atlas. The Journal of Physical Chemistry Letters 2015, 6 (16) , 3228-3235. https://doi.org/10.1021/acs.jpclett.5b01154
    46. Zebing Zeng, Sangsu Lee, Minjung Son, Kotaro Fukuda, Paula Mayorga Burrezo, Xiaojian Zhu, Qingbiao Qi, Run-Wei Li, Juan T. López Navarrete, Jun Ding, Juan Casado, Masayoshi Nakano, Dongho Kim, and Jishan Wu . Push–Pull Type Oligo(N-annulated perylene)quinodimethanes: Chain Length and Solvent-Dependent Ground States and Physical Properties. Journal of the American Chemical Society 2015, 137 (26) , 8572-8583. https://doi.org/10.1021/jacs.5b04156
    47. Junzhi Liu, Bo-Wei Li, Yuan-Zhi Tan, Angelos Giannakopoulos, Carlos Sanchez-Sanchez, David Beljonne, Pascal Ruffieux, Roman Fasel, Xinliang Feng, and Klaus Müllen . Toward Cove-Edged Low Band Gap Graphene Nanoribbons. Journal of the American Chemical Society 2015, 137 (18) , 6097-6103. https://doi.org/10.1021/jacs.5b03017
    48. Paula Mayorga Burrezo, Xiaozhang Zhu, Shou-Fei Zhu, Qifan Yan, Juan T. López Navarrete, Hayato Tsuji, Eiichi Nakamura, and Juan Casado . Planarization, Fusion, and Strain of Carbon-Bridged Phenylenevinylene Oligomers Enhance π-Electron and Charge Conjugation: A Dissectional Vibrational Raman Study. Journal of the American Chemical Society 2015, 137 (11) , 3834-3843. https://doi.org/10.1021/ja5125463
    49. Kyoung Chul Ko, Young Geun Park, Daeheum Cho, and Jin Yong Lee . Simple but Useful Scheme toward Understanding of Intramolecular Magnetic Interactions: Benzene-Bridged Oxoverdazyl Diradicals. The Journal of Physical Chemistry A 2014, 118 (40) , 9596-9606. https://doi.org/10.1021/jp5072007
    50. Zhe Sun, Zebing Zeng, and Jishan Wu . Zethrenes, Extended p-Quinodimethanes, and Periacenes with a Singlet Biradical Ground State. Accounts of Chemical Research 2014, 47 (8) , 2582-2591. https://doi.org/10.1021/ar5001692
    51. Qun Ye and Chunyan Chi . Recent Highlights and Perspectives on Acene Based Molecules and Materials. Chemistry of Materials 2014, 26 (14) , 4046-4056. https://doi.org/10.1021/cm501536p
    52. Masahiko Iyoda, Keita Tanaka, Hideyuki Shimizu, Masashi Hasegawa, Tohru Nishinaga, Tomohiko Nishiuchi, Yoshihito Kunugi, Takayuki Ishida, Hiroyuki Otani, Hiroyasu Sato, Koji Inukai, Kazukuni Tahara, and Yoshito Tobe . Multifunctional π-Expanded Macrocyclic Oligothiophene 6-Mers and Related Macrocyclic Oligomers. Journal of the American Chemical Society 2014, 136 (6) , 2389-2396. https://doi.org/10.1021/ja4101744
    53. Zhe Sun, Sangsu Lee, Kyu Hyung Park, Xiaojian Zhu, Wenhua Zhang, Bin Zheng, Pan Hu, Zebing Zeng, Soumyajit Das, Yuan Li, Chunyan Chi, Run-Wei Li, Kuo-Wei Huang, Jun Ding, Dongho Kim, and Jishan Wu . Dibenzoheptazethrene Isomers with Different Biradical Characters: An Exercise of Clar’s Aromatic Sextet Rule in Singlet Biradicaloids. Journal of the American Chemical Society 2013, 135 (48) , 18229-18236. https://doi.org/10.1021/ja410279j
    54. Manabu Abe . Diradicals. Chemical Reviews 2013, 113 (9) , 7011-7088. https://doi.org/10.1021/cr400056a
    55. Katsuki Okuno, Yasuteru Shigeta, Ryohei Kishi, and Masayoshi Nakano . Photochromic Switching of Diradical Character: Design of Efficient Nonlinear Optical Switches. The Journal of Physical Chemistry Letters 2013, 4 (15) , 2418-2422. https://doi.org/10.1021/jz401228c
    56. Masayoshi Takase, Tomoyuki Narita, Wataru Fujita, Motoko S. Asano, Tohru Nishinaga, Hiroaki Benten, Kenji Yoza, and Klaus Müllen . Pyrrole-Fused Azacoronene Family: The Influence of Replacement with Dialkoxybenzenes on the Optical and Electronic Properties in Neutral and Oxidized States. Journal of the American Chemical Society 2013, 135 (21) , 8031-8040. https://doi.org/10.1021/ja402371f
    57. Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Ryohei Kishi, Yasuteru Shigeta, Masayoshi Nakano, Kazuya Tokunaga, Kenji Kamada, and Takashi Kubo . Synthesis and Characterization of Quarteranthene: Elucidating the Characteristics of the Edge State of Graphene Nanoribbons at the Molecular Level. Journal of the American Chemical Society 2013, 135 (4) , 1430-1437. https://doi.org/10.1021/ja309599m
    58. Jens Antony, Bassam Alameddine, Titus A. Jenny, and Stefan Grimme . Theoretical Study of the Stacking Behavior of Selected Polycondensed Aromatic Hydrocarbons with Various Symmetries. The Journal of Physical Chemistry A 2013, 117 (3) , 616-625. https://doi.org/10.1021/jp3075207
    59. Wataru Mizukami, Yuki Kurashige, and Takeshi Yanai . More π Electrons Make a Difference: Emergence of Many Radicals on Graphene Nanoribbons Studied by Ab Initio DMRG Theory. Journal of Chemical Theory and Computation 2013, 9 (1) , 401-407. https://doi.org/10.1021/ct3008974
    60. Kyohei Yoneda, Masayoshi Nakano, Kotaro Fukuda, and Benoît Champagne . The Odd Electron Density Is the Guide toward Achieving Organic Molecules with Gigantic Third-Order Nonlinear Optical Responses. The Journal of Physical Chemistry Letters 2012, 3 (22) , 3338-3342. https://doi.org/10.1021/jz301573j
    61. Soichi Ito, Takuya Minami, and Masayoshi Nakano . Diradical Character Based Design for Singlet Fission of Condensed-Ring Systems with 4nπ Electrons. The Journal of Physical Chemistry C 2012, 116 (37) , 19729-19736. https://doi.org/10.1021/jp3072684
    62. Yuan Li, Wee-Kuan Heng, Byung Sun Lee, Naoki Aratani, José L. Zafra, Nina Bao, Richmond Lee, Young Mo Sung, Zhe Sun, Kuo-Wei Huang, Richard D. Webster, Juan T. López Navarrete, Dongho Kim, Atsuhiro Osuka, Juan Casado, Jun Ding, and Jishan Wu . Kinetically Blocked Stable Heptazethrene and Octazethrene: Closed-Shell or Open-Shell in the Ground State?. Journal of the American Chemical Society 2012, 134 (36) , 14913-14922. https://doi.org/10.1021/ja304618v
    63. Zebing Zeng, Young Mo Sung, Nina Bao, Davin Tan, Richmond Lee, José L. Zafra, Byung Sun Lee, Masatoshi Ishida, Jun Ding, Juan T. López Navarrete, Yuan Li, Wangdong Zeng, Dongho Kim, Kuo-Wei Huang, Richard D. Webster, Juan Casado, and Jishan Wu . Stable Tetrabenzo-Chichibabin’s Hydrocarbons: Tunable Ground State and Unusual Transition between Their Closed-Shell and Open-Shell Resonance Forms. Journal of the American Chemical Society 2012, 134 (35) , 14513-14525. https://doi.org/10.1021/ja3050579
    64. Kyohei Yoneda, Masayoshi Nakano, Yudai Inoue, Tomoya Inui, Kotaro Fukuda, and Yasuteru Shigeta , Takashi Kubo , Benoît Champagne . Impact of Antidot Structure on the Multiradical Characters, Aromaticities, and Third-Order Nonlinear Optical Properties of Hexagonal Graphene Nanoflakes. The Journal of Physical Chemistry C 2012, 116 (33) , 17787-17795. https://doi.org/10.1021/jp305171k
    65. Masakazu Makino and Jun-ichi Aihara . Macrocyclic Aromaticity of Porphyrin Units in Fully Conjugated Oligoporphyrins. The Journal of Physical Chemistry A 2012, 116 (30) , 8074-8084. https://doi.org/10.1021/jp304681h
    66. Gary J. Snyder . Rational Design of High-Spin Biradicaloids in the Isobenzofulvene and Isobenzoheptafulvene Series. The Journal of Physical Chemistry A 2012, 116 (21) , 5272-5291. https://doi.org/10.1021/jp304015k
    67. Takuya Minami and Masayoshi Nakano . Diradical Character View of Singlet Fission. The Journal of Physical Chemistry Letters 2012, 3 (2) , 145-150. https://doi.org/10.1021/jz2015346
    68. Jerry Ray Dias . Valence-Bond Determination of Bond Lengths of Polycyclic Aromatic Hydrocarbons: Comparisons with Recent Experimental and Ab Initio Results. The Journal of Physical Chemistry A 2011, 115 (46) , 13619-13627. https://doi.org/10.1021/jp207531u
    69. Xiaozhang Zhu, Hayato Tsuji, Koji Nakabayashi, Shin-ichi Ohkoshi, and Eiichi Nakamura . Air- and Heat-Stable Planar Tri-p-quinodimethane with Distinct Biradical Characteristics. Journal of the American Chemical Society 2011, 133 (41) , 16342-16345. https://doi.org/10.1021/ja206060n
    70. Masatoshi Ishida, Jae-Yoon Shin, Jong Min Lim, Byung Sun Lee, Min-Chul Yoon, Taro Koide, Jonathan L. Sessler, Atsuhiro Osuka, and Dongho Kim . Neutral Radical and Singlet Biradical Forms of Meso-Free, -Keto, and -Diketo Hexaphyrins(1.1.1.1.1.1): Effects on Aromaticity and Photophysical Properties. Journal of the American Chemical Society 2011, 133 (39) , 15533-15544. https://doi.org/10.1021/ja204626t
    71. Masayoshi Nakano, Ryohei Kishi, Kyohei Yoneda, Yudai Inoue, Tomoya Inui, and Yasuteru Shigeta , Takashi Kubo , Benoît Champagne . Third-Order Nonlinear Optical Properties of Open-Shell Supermolecular Systems Composed of Acetylene Linked Phenalenyl Radicals. The Journal of Physical Chemistry A 2011, 115 (31) , 8767-8777. https://doi.org/10.1021/jp205259p
    72. Zhe Sun, Kuo-Wei Huang, and Jishan Wu . Soluble and Stable Heptazethrenebis(dicarboximide) with a Singlet Open-Shell Ground State. Journal of the American Chemical Society 2011, 133 (31) , 11896-11899. https://doi.org/10.1021/ja204501m
    73. Xingfa Gao, Jennifer L. Hodgson, De-en Jiang, Shengbai B. Zhang, Shigeru Nagase, Glen P. Miller, and Zhongfang Chen . Open-Shell Singlet Character of Stable Derivatives of Nonacene, Hexacene and Teranthene. Organic Letters 2011, 13 (13) , 3316-3319. https://doi.org/10.1021/ol201004u
    74. Masayoshi Nakano, Takuya Minami, Kyohei Yoneda, Shabbir Muhammad, Ryohei Kishi, Yasuteru Shigeta, Takashi Kubo, Léa Rougier, Benoît Champagne, Kenji Kamada, and Koji Ohta . Giant Enhancement of the Second Hyperpolarizabilities of Open-Shell Singlet Polyaromatic Diphenalenyl Diradicaloids by an External Electric Field and Donor–Acceptor Substitution. The Journal of Physical Chemistry Letters 2011, 2 (9) , 1094-1098. https://doi.org/10.1021/jz200383a
    75. Ryohei Kishi and Masayoshi Nakano . Quantum Master Equation Method Based on the Broken-Symmetry Time-Dependent Density Functional Theory: Application to Dynamic Polarizability of Open-Shell Molecular Systems. The Journal of Physical Chemistry A 2011, 115 (15) , 3565-3575. https://doi.org/10.1021/jp200056m
    76. Simone Di Motta, Fabrizia Negri, Daniele Fazzi, Chiara Castiglioni, and Eleonora Valeria Canesi . Biradicaloid and Polyenic Character of Quinoidal Oligothiophenes Revealed by the Presence of a Low-Lying Double-Exciton State. The Journal of Physical Chemistry Letters 2010, 1 (23) , 3334-3339. https://doi.org/10.1021/jz101400d
    77. Shuichi Suzuki, Takanori Furui, Masato Kuratsu, Masatoshi Kozaki, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, and Keiji Okada. Nitroxide-Substituted Nitronyl Nitroxide and Iminonitroxide. Journal of the American Chemical Society 2010, 132 (45) , 15908-15910. https://doi.org/10.1021/ja107769z
    78. Xinyu Tian, Jiaxiang Guo, Zeyi Li, Shihou Sheng, Tianyu Zhang, Xianfei Li, Chuandong Dou. Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion. Chinese Chemical Letters 2025, 36 (1) , 110174. https://doi.org/10.1016/j.cclet.2024.110174
    79. Xin Li, Zhen Xu, Donglei Bu, Jinming Cai, Huamei Chen, Qi Chen, Ting Chen, Fang Cheng, Lifeng Chi, Wenjie Dong, Zhenchao Dong, Shixuan Du, Qitang Fan, Xing Fan, Qiang Fu, Song Gao, Jing Guo, Weijun Guo, Yang He, Shimin Hou, Ying Jiang, Huihui Kong, Baojun Li, Dengyuan Li, Jie Li, Qing Li, Ruoning Li, Shuying Li, Yuxuan Lin, Mengxi Liu, Peinian Liu, Yanyan Liu, Jingtao Lü, Chuanxu Ma, Haoyang Pan, JinLiang Pan, Minghu Pan, Xiaohui Qiu, Ziyong Shen, Qiang Sun, Shijing Tan, Bing Wang, Dong Wang, Li Wang, Lili Wang, Tao Wang, Xiang Wang, Xingyue Wang, Xueyan Wang, Yansong Wang, Yu Wang, Kai Wu, Wei Xu, Na Xue, Linghao Yan, Fan Yang, Zhiyong Yang, Chi Zhang, Xue Zhang, Yang Zhang, Yao Zhang, Xiong Zhou, Junfa Zhu, Yajie Zhang, Feixue Gao, Yongfeng Wang. Recent progress on surface chemistry II: Property and characterization. Chinese Chemical Letters 2025, 36 (1) , 110100. https://doi.org/10.1016/j.cclet.2024.110100
    80. xiushang xu, Liliia Moshniaha, Serhii Vasylevskyi, Ryota Kabe, Tatsuhiko Ohto, Akimitsu Narita. Synthesis and Characterizations of Dibenzo‐Fused Perioctacene. Angewandte Chemie 2024, https://doi.org/10.1002/ange.202418334
    81. xiushang xu, Liliia Moshniaha, Serhii Vasylevskyi, Ryota Kabe, Tatsuhiko Ohto, Akimitsu Narita. Synthesis and Characterizations of Dibenzo‐Fused Perioctacene. Angewandte Chemie International Edition 2024, https://doi.org/10.1002/anie.202418334
    82. Qing Jiang, Yi Han, Xudong Hou, Shaofei Wu, Tingting Xu, Mesías Orozco-Ic, Gabriel Merino, Chunyan Chi. Dicyclopenta[4,3,2,1‐cde:4',3',2',1'‐pqr]‐peri‐tetracene: Synthesis and An Example of Annulene‐Within‐An‐Annulene Aromaticity in Different Redox States. Angewandte Chemie International Edition 2024, https://doi.org/10.1002/anie.202416833
    83. Qing Jiang, Yi Han, Xudong Hou, Shaofei Wu, Tingting Xu, Mesías Orozco-Ic, Gabriel Merino, Chunyan Chi. Dicyclopenta[4,3,2,1‐cde:4',3',2',1'‐pqr]‐peri‐tetracene: Synthesis and An Example of Annulene‐Within‐An‐Annulene Aromaticity in Different Redox States. Angewandte Chemie 2024, https://doi.org/10.1002/ange.202416833
    84. María Privado, Sergio Moles Quintero, Myriam Barrejón, Pilar de La Cruz, Janaarthana Babu P. M., David Casanova, Fernando Langa, Juan Casado. Dibenzoquinone Cyclopentadithiophene Diradicaloids Show Optical Transitions of Different Spin States and Anomalous Near‐Infrared Emission. Angewandte Chemie International Edition 2024, 30 https://doi.org/10.1002/anie.202413988
    85. María Privado, Sergio Moles Quintero, Myriam Barrejón, Pilar de La Cruz, Janaarthana Babu P. M., David Casanova, Fernando Langa, Juan Casado. Dibenzoquinone Cyclopentadithiophene Diradicaloids Show Optical Transitions of Different Spin States and Anomalous Near‐Infrared Emission. Angewandte Chemie 2024, 30 https://doi.org/10.1002/ange.202413988
    86. Qing Jiang, Yi Han, Shaofei Wu, Tingting Xu, Chunyan Chi. Dibenzo‐ peri ‐Heptacene: A Stable Open‐Shell Graphene Fragment With a Balanced Combination of Armchair and Zigzag Edge Structures. Small 2024, 2 https://doi.org/10.1002/smll.202404762
    87. Gibu George, Anton J. Stasyuk, Miquel Solà. Prediction of the ground state for indenofluorene-type systems with Clar's π-sextet model. Chemical Science 2024, 15 (34) , 13676-13687. https://doi.org/10.1039/D4SC03465A
    88. Jingyuan Yang, Xinyu Tian, Liuzhong Yuan, Yu Liu, Yue Wang, Chuandong Dou. Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters 2024, 35 (8) , 109745. https://doi.org/10.1016/j.cclet.2024.109745
    89. Mahmoud A.S. Sakr, Omar H. Abd-Elkader, Hazem Abdelsalam, Qinfang Zhang. Magnetic properties of laterally connected super-zethrene chains: Insights from spin-polarized calculations. Journal of Magnetism and Magnetic Materials 2024, 590 , 171684. https://doi.org/10.1016/j.jmmm.2023.171684
    90. Qing Jiang, Hui Tang, Yuchen Peng, Zhenni Hu, Wangdong Zeng. Helical polycyclic hydrocarbons with open-shell singlet ground states and ambipolar redox behaviors. Chemical Science 2024, 6 https://doi.org/10.1039/D4SC02116A
    91. Himanshu Sharma, Palash Jana, Dibyendu Mallick, Subhajit Bandyopadhyay, Soumyajit Das. 6,6′-Biindeno[1,2- b ]fluorene: an open-shell indenofluorene dimer. Chemical Science 2024, 146 https://doi.org/10.1039/D4SC03996C
    92. Hui Zhang, Jianchen Lu, Xin‐Jing Zhao, Baijin Li, Hangjing Zhou, Yong Zhang, Gefei Niu, Boyu Fu, Lei Gao, Yuan‐Zhi Tan, Jinming Cai. Length‐Dependent Magnetic Evolution of Anthenes on Au(111). Angewandte Chemie International Edition 2023, 62 (52) https://doi.org/10.1002/anie.202315216
    93. Hui Zhang, Jianchen Lu, Xin‐Jing Zhao, Baijin Li, Hangjing Zhou, Yong Zhang, Gefei Niu, Boyu Fu, Lei Gao, Yuan‐Zhi Tan, Jinming Cai. Length‐Dependent Magnetic Evolution of Anthenes on Au(111). Angewandte Chemie 2023, 135 (52) https://doi.org/10.1002/ange.202315216
    94. Jin‐Jiang Zhang, Lin Yang, Fupin Liu, Gianluca Serra, Yubin Fu, Andrea Lucotti, Alexey A. Popov, Matteo Tommasini, Ji Ma, Xinliang Feng. Pushing Up the Size Limit of Boron‐doped peri ‐Acenes: Modular Synthesis and Characterizations. Angewandte Chemie 2023, 135 (48) https://doi.org/10.1002/ange.202312055
    95. Jin‐Jiang Zhang, Lin Yang, Fupin Liu, Gianluca Serra, Yubin Fu, Andrea Lucotti, Alexey A. Popov, Matteo Tommasini, Ji Ma, Xinliang Feng. Pushing Up the Size Limit of Boron‐doped peri ‐Acenes: Modular Synthesis and Characterizations. Angewandte Chemie International Edition 2023, 62 (48) https://doi.org/10.1002/anie.202312055
    96. Gabriela Borin Barin, Marco Di Giovannantonio, Thorsten G. Lohr, Shantanu Mishra, Amogh Kinikar, Mickael L. Perrin, Jan Overbeck, Michel Calame, Xinliang Feng, Roman Fasel, Pascal Ruffieux. On-surface synthesis and characterization of teranthene and hexanthene: ultrashort graphene nanoribbons with mixed armchair and zigzag edges. Nanoscale 2023, 15 (41) , 16766-16774. https://doi.org/10.1039/D3NR03736C
    97. Shahram MohammadNejad, Pouya Nosratkhah, Hossein Arab. Recent advances in room temperature single-photon emitters. Quantum Information Processing 2023, 22 (10) https://doi.org/10.1007/s11128-023-04100-3
    98. Qing Jiang, Haipeng Wei, Xudong Hou, Chunyan Chi. Circumpentacene with Open‐Shell Singlet Diradical Character. Angewandte Chemie 2023, 135 (35) https://doi.org/10.1002/ange.202306938
    99. Qing Jiang, Haipeng Wei, Xudong Hou, Chunyan Chi. Circumpentacene with Open‐Shell Singlet Diradical Character. Angewandte Chemie International Edition 2023, 62 (35) https://doi.org/10.1002/anie.202306938
    100. Zeyi Li, Tingting Sun, Jiaxiang Guo, Xinyu Tian, Yujia Liu, Shihou Sheng, Kaiqi Ye, Zhigang Xie, Chuandong Dou. Ladder-type boron-containing π-systems with enhanced open-shell characteristics and photothermal conversion properties. Organic Chemistry Frontiers 2023, 10 (17) , 4289-4297. https://doi.org/10.1039/D3QO00900A
    Load more citations

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2010, 132, 32, 11021–11023
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja1049737
    Published July 26, 2010
    Copyright © 2010 American Chemical Society

    Article Views

    8927

    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.