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Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 507-517

http://dx.doi.org/10.1351/pac200880030507

Oxophenalenoxyl: Novel stable neutral radicals with a unique spin-delocalized nature depending on topological symmetries and redox states

Yasushi Morita1,2, Shinsuke Nishida3, Junya Kawai1, Takeji Takui3 and Kazuhiro Nakasuji1

1 Department of Chemistry, Osaka University, Toyonaka, Osaka 560-0043, Japan
2 PRESTO, Japan Science and Technology Agency, Honcho, Kawaguchi, Saitama 332-0012, Japan
3 Departments of Chemistry and Materials Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan

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  • Nishida Shinsuke, Fukui Kozo, Morita Yasushi: Hydrogen-Bonding Effect on Spin-Center Transfer of Tetrathiafulvalene-Linked 6-Oxophenalenoxyl Evaluated Using Temperature-Dependent Cyclic Voltammetry and Theoretical Calculations. Chem. Asian J. 2014, 9, 500. <http://dx.doi.org/10.1002/asia.201301188>
  • Ueda Akira, Wasa Hideki, Nishida Shinsuke, Kanzaki Yuki, Sato Kazunobu, Takui Takeji, Morita Yasushi: A Dicyanomethylene-Substituted Triangulene: Effects of Molecular-Symmetry Reduction and Electron-Accepting Substituents on a Fused Polycyclic Neutral π-Radical System. Chem. Asian J. 2013, 8, 2057. <http://dx.doi.org/10.1002/asia.201300471>
  • Cirera Borja, Zhang Yi-Qi, Klyatskaya Svetlana, Ruben Mario, Klappenberger Florian, Barth Johannes V.: 2 D Self-Assembly and Catalytic Homo-coupling of the Terminal Alkyne 1,4-Bis(3,5-diethynyl-phenyl)butadiyne-1,3 on Ag(111). ChemCatChem 2013, 5, 3281. <http://dx.doi.org/10.1002/cctc.201300299>
  • Nishida Shinsuke, Kawai Junya, Moriguchi Miki, Ohba Tomohiro, Haneda Naoki, Fukui Kozo, Fuyuhiro Akira, Shiomi Daisuke, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita Yasushi: Control of Exchange Interactions in π Dimers of 6-Oxophenalenoxyl Neutral π Radicals: Spin-Density Distributions and Multicentered-Two-Electron Bonding Governed by Topological Symmetry and Substitution at the 8-Position. Chem. Eur. J. 2013, 19, 11904. <http://dx.doi.org/10.1002/chem.201301783>
  • Morita Yasushi, Murata Tsuyoshi, Nakasuji Kazuhiro: Cooperation of Hydrogen-Bond and Charge-Transfer Interactions in Molecular Complexes in the Solid State. Bull. Chem. Soc. Jpn. 2013, 183. <http://dx.doi.org/10.1246/bcsj.20120241>
  • Ueda Akira, Wasa Hideki, Nishida Shinsuke, Kanzaki Yuki, Sato Kazunobu, Shiomi Daisuke, Takui Takeji, Morita Yasushi: An Extremely Redox-Active Air-Stable Neutral π Radical: Dicyanomethylene-Substituted Triangulene with a Threefold Symmetry. Chem. Eur. J. 2012, 18, 16272. <http://dx.doi.org/10.1002/chem.201203755>
  • Bag Pradip, Itkis Mikhail E., Pal Sushanta K., Bekyarova Elena, Donnadieu Bruno, Haddon Robert C.: Synthesis, structure and solid state properties of benzannulated phenalenyl based neutral radical conductor. J. Phys. Org. Chem. 2012, 25, 566. <http://dx.doi.org/10.1002/poc.2906>
  • Murata Tsuyoshi, Miyazaki Eigo, Yokoyama Takuji, Nakasuji Kazuhiro, Morita Yasushi: Intermolecular Hydrogen-Bond Networks and Physical Properties of BF4– and TCNQ•– Salts of Three-Fold Symmetric Tris(alkylamino)phenalenyliums. Growth Des 2012, 12, 804. <http://dx.doi.org/10.1021/cg201120s>
  • Ratera Imma, Veciana Jaume: Playing with organic radicals as building blocks for functional molecular materials. Chemical Society Review 2012, 41, 303. <http://dx.doi.org/10.1039/c1cs15165g>
  • Nishida  Shinsuke, Kariyazono Kazuki, Yamanaka Azusa, Fukui Kozo, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita Yasushi: Electronic Stabilization Effect of a Spin-Delocalized Neutral Radical: Synthesis of an 8-Cyano-6-oxophenalenoxyl Derivative and Quantitative Evaluation of the Electronic Spin Structure in terms of Resonance Structures. Chem. Asian J. 2011, 6, 1188. <http://dx.doi.org/10.1002/asia.201000793>
  • Yakiyama Yumi, Murata Tsuyoshi, Ise Tomoaki, Shiomi Daisuke, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita Yasushi: Solution-Stable Triple Helicates of Quaterimidazole: Three-Dimensional Crystal Structures and Optical Resolution by Chiral-Column HPLC. Eur J Inorg Chem 2011, 2011, 3438. <http://dx.doi.org/10.1002/ejic.201100488>
  • Ueda Akira, Yoshida Kenta, Suzuki Shuichi, Fukui Kozo, Nakasuji Kazuhiro, Morita Yasushi: Heteroatom functionalization of phenalenyl: synthesis, structures, and properties of hexa-substituted phenalenyliums : HETEROATOM FUNCTIONALIZATION OF PHENALENYL. J  Phys Org Chem 2011, 24, 952. <http://dx.doi.org/10.1002/poc.1916>
  • Hou Yanhui, Wang Huikai, Li Zhi, Liu Yongsheng, Wan Xiangjian, Xue Xiaosong, Chen Yongsheng, Yu Ao: Organic radicals based on phenalenyl and verdazyl units. Tetrahedron Letters 2011, 52, 3670. <http://dx.doi.org/10.1016/j.tetlet.2011.05.031>
  • Geldof D., Krishtal A., Blockhuys F., Van Alsenoy C.: An Extension of the Hirshfeld Method to Open Shell Systems Using Fractional Occupations. J Chem Theory Comput 2011, 7, 1328. <http://dx.doi.org/10.1021/ct100743h>
  • Morita Yasushi, Suzuki Shuichi, Sato Kazunobu, Takui Takeji: Synthetic organic spin chemistry for structurally well-defined open-shell graphene fragments. Nature Chem 2011, 3, 197. <http://dx.doi.org/10.1038/nchem.985>
  • Morita Yasushi, Nishida Shinsuke, Murata Tsuyoshi, Moriguchi Miki, Ueda Akira, Satoh Masaharu, Arifuku Kazunori, Sato Kazunobu, Takui Takeji: Organic tailored batteries materials using stable open-shell molecules with degenerate frontier orbitals. nat mat 2011, 10, 947. <http://dx.doi.org/10.1038/nmat3142>
  • Ueda Akira, Nishida Shinsuke, Fukui Kozo, Ise Tomoaki, Shiomi Daisuke, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita  Yasushi: Three-Dimensional Intramolecular Exchange Interaction in a Curved and Nonalternant π-Conjugated System: Corannulene with Two Phenoxyl Radicals. angew chemie 2010, 122, 1722. <http://dx.doi.org/10.1002/ange.200906666>
  • Ueda Akira, Ogasawara Kanako, Nishida Shinsuke, Ise Tomoaki, Yoshino Tomohiro, Nakazawa Shigeaki, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita Yasushi: A Bowl-Shaped ortho-Semiquinone Radical Anion: Quantitative Evaluation of the Dynamic Behavior of Structural and Electronic Features. Angew Chem 2010, 122, 6477. <http://dx.doi.org/10.1002/ange.201002626>
  • Ueda Akira, Nishida Shinsuke, Fukui Kozo, Ise Tomoaki, Shiomi Daisuke, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita  Yasushi: Three-Dimensional Intramolecular Exchange Interaction in a Curved and Nonalternant π-Conjugated System: Corannulene with Two Phenoxyl Radicals. Angew Chem Int E 2010, 49, 1678. <http://dx.doi.org/10.1002/anie.200906666>
  • Ueda Akira, Ogasawara Kanako, Nishida Shinsuke, Ise Tomoaki, Yoshino Tomohiro, Nakazawa Shigeaki, Sato Kazunobu, Takui Takeji, Nakasuji Kazuhiro, Morita Yasushi: A Bowl-Shaped ortho-Semiquinone Radical Anion: Quantitative Evaluation of the Dynamic Behavior of Structural and Electronic Features. Angew Chem Int Ed 2010, 49, 6333. <http://dx.doi.org/10.1002/anie.201002626>