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Pure Appl. Chem., 2010, Vol. 82, No. 4, pp. 871-878

http://dx.doi.org/10.1351/PAC-CON-09-10-12

Published online 2010-03-10

Tetradehydrodinaphtho[10]annulene and its transformation into zethrene: A hitherto unknown dehydroannulene and a forgotten aromatic hydrocarbon

Rui Umeda, Daijiro Hibi, Koji Miki and Yoshito Tobe*

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

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  • Nakano Masayoshi, Kishi Ryohei, Fukui Hitoshi, Minami Takuya, Yoneda Kyohei, Minamide Shu, Inoue Yudai, Yamada Taishi, Ito Soichi, Muhammad Shabbir, Shigeta Yasuteru, Kubo Takashi, Champagne Benoît: Diradicalology in third-order nonlinear optical systems: Second hyperpolarizabilities of acetylene-linked phenalenyl-based superpolyenes. Int. J. Quantum Chem. 2013, 113, 585. <http://dx.doi.org/10.1002/qua.24035>
  • Fukazawa Aiko, Oshima Hiroya, Shiota Yoshihito, Takahashi Shouya, Yoshizawa Kazunari, Yamaguchi Shigehiro: Thiophene-Fused Bisdehydro[12]annulene That Undergoes Transannular Alkyne Cycloaddition by Either Light or Heat. J. Am. Chem. Soc. 2013, 135, 1731. <http://dx.doi.org/10.1021/ja3126849>
  • Sun Zhe, Wu Jishan: 7,14-Diaryl-Substituted Zethrene Diimides as Stable Far-Red Dyes with Tunable Photophysical Properties. J. Org. Chem. 2013, 78, 9032. <http://dx.doi.org/10.1021/jo401061g>
  • Hibi Daijiro, Kitabayashi Kenichi, Shimizu Akihiro, Umeda Rui, Tobe Yoshito: Synthesis and physical properties of zethrene derivatives bearing donor/acceptor substituents at 7,14-positions. Org. Biomol. Chem. 2013, 11, 8256. <http://dx.doi.org/10.1039/c3ob41674g>
  • Shan Liang, Liang Zhixiong, Xu Xiaomin, Tang Qin, Miao Qian: Revisiting zethrene: synthesis, reactivity and semiconductor properties. Chem. Sci. 2013, 4, 3294. <http://dx.doi.org/10.1039/c3sc51158h>
  • Nakano Masayoshi, Champagne Benoı̂t: Diradical character dependences of the first and second hyperpolarizabilities of asymmetric open-shell singlet systems. J. Chem. Phys. 2013, 138, 244306. <http://dx.doi.org/10.1063/1.4810860>
  • Nishida Jun-ichi, Tsukaguchi Shingo, Yamashita Yoshiro: Synthesis, Crystal Structures, and Properties of 6,12-Diaryl-Substituted Indeno[1,2-b]fluorenes. Chem. Eur. J. 2012, 18, 8964. <http://dx.doi.org/10.1002/chem.201200591>
  • Sun Zhe, Wu Jishan: Open-shell polycyclic aromatic hydrocarbons. J Materials Chemistry 2012, 22, 4151. <http://dx.doi.org/10.1039/c1jm14786b>
  • Sun Zhe, Ye Qun, Chi Chunyan, Wu Jishan: Low band gap polycyclic hydrocarbons: from closed-shell near infrared dyes and semiconductors to open-shell radicals. Chem. Soc. Rev. 2012, 41, 7857. <http://dx.doi.org/10.1039/c2cs35211g>
  • Nakano Masayoshi, Minami Takuya, Fukui Hitoshi, Kishi Ryohei, Shigeta Yasuteru, Champagne Benoı̂t: Full configuration interaction calculations of the second hyperpolarizabilities of the H4 model compound: Summation-over-states analysis and interplay with diradical characters. Journal Chemical Physics 2012, 136, 024315. <http://dx.doi.org/10.1063/1.3675684>
  • Shimizu Akihiro, Tobe Yoshito: Indeno[2,1-a]fluorene: An Air-Stable ortho-Quinodimethane Derivative. angew chemie 2011, 123, 7038. <http://dx.doi.org/10.1002/ange.201101950>
  • Shimizu Akihiro, Tobe Yoshito: Indeno[2,1-a]fluorene: An Air-Stable ortho-Quinodimethane Derivative. Angew Chem Int E 2011, 50, 6906. <http://dx.doi.org/10.1002/anie.201101950>
  • Huang Xiaobo, Zeng Lintao, Zeng Zebing, Wu Jishan: Intramolecular Domino Electrophilic and Thermal Cyclization of peri-Ethynylene Naphthalene Oligomers. Chemistry A European Journal 2011, 17, 14907. <http://dx.doi.org/10.1002/chem.201102506>
  • Sun Zhe, Huang Kuo-Wei, Wu Jishan: Soluble and Stable Heptazethrenebis(dicarboximide) with a Singlet Open-Shell Ground State. J Am Chcm Soc 2011, 133, 11896. <http://dx.doi.org/10.1021/ja204501m>
  • Kishi Ryohei, Nakano Masayoshi: Quantum Master Equation Method Based on the Broken-Symmetry Time-Dependent Density Functional Theory: Application to Dynamic Polarizability of Open-Shell Molecular Systems. J Phys Chem A 2011, 115, 3565. <http://dx.doi.org/10.1021/jp200056m>
  • Nakano Masayoshi, Kishi Ryohei, Yoneda Kyohei, Inoue Yudai, Inui Tomoya, Shigeta Yasuteru, Kubo Takashi, Champagne Benoît: Third-Order Nonlinear Optical Properties of Open-Shell Supermolecular Systems Composed of Acetylene Linked Phenalenyl Radicals. J Phys Chem A 2011, 115, 8767. <http://dx.doi.org/10.1021/jp205259p>
  • Wu Tsun-Cheng, Chen Chia-Hua, Hibi Daijiro, Shimizu Akihiro, Tobe Yoshito, Wu Yao-Ting: Synthesis, Structure, and Photophysical Properties of Dibenzo[de,mn]naphthacenes. Angew Chem 2010, 122, 7213. <http://dx.doi.org/10.1002/ange.201001929>
  • Wu Tsun-Cheng, Chen Chia-Hua, Hibi Daijiro, Shimizu Akihiro, Tobe Yoshito, Wu Yao-Ting: Synthesis, Structure, and Photophysical Properties of Dibenzo[de,mn]naphthacenes. Angew Chem Int Ed 2010, 49, 7059. <http://dx.doi.org/10.1002/anie.201001929>
  • Umeda Rui, Hibi Daijiro, Miki Koji, Tobe Yoshito: ChemInform Abstract: Tetradehydrodinaphtho[10]annulene and Its Transformation into Zethrene: A Hitherto Unknown Dehydroannulene and a Forgotten Aromatic Hydrocarbon. ChemInform 2010, 41, no. <http://dx.doi.org/10.1002/chin.201041258>