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Indeno[2,1-b]fluorene: A 20-π-Electron Hydrocarbon with Very Low-Energy Light Absorption

Authors

  • Dr. Akihiro Shimizu,

    1. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)
    2. Present address: Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto (Japan)
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  • Dr. Ryohei Kishi,

    1. Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Osaka (Japan)
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  • Prof. Masayoshi Nakano,

    1. Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Osaka (Japan)
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  • Dr. Daisuke Shiomi,

    1. Department of Chemistry, Graduate School of Science, Osaka City University, Osaka (Japan)
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  • Prof. Kazunobu Sato,

    1. Department of Chemistry, Graduate School of Science, Osaka City University, Osaka (Japan)
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  • Prof. Takeji Takui,

    1. Department of Chemistry, Graduate School of Science, Osaka City University, Osaka (Japan)
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  • Dr. Ichiro Hisaki,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Osaka (Japan)
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  • Prof. Mikiji Miyata,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Osaka (Japan)
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  • Prof. Yoshito Tobe

    Corresponding author
    1. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)
    • Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531 (Japan)

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  • This work was supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan), “Quantum Cybernetics”, FIRST project on QIP, JSPS and a Sasakawa Scientific Research Grant from the Japan Science Society. The authors acknowledge Prof. T. Kubo of Osaka University (Japan) for the use of facilities and valuable discussions, Prof. S. Ito and J. Takaichi of Osaka University (Japan) for the use of a spectrometer, and Prof. B. Champagne of Facultés Universitaires Notre-Dame de la Paix (FUNDP), Belgium for the use of computers and the program for the theoretical calculations. The synchrotron radiation experiments were performed at the BL38B1 of SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI; proposal No. 2011A1341). The authors are grateful to Dr. K. Miura, Dr. S. Baba, and Dr. N. Mizuno for crystallographic data collection.

Abstract

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Smaller can be better: The first example of meta-quinodimethane embedded in an indenofluorene framework has been synthesized. 10,12-Dimesitylindeno[2,1-b]fluorene exhibits extremely low-energy light absorption, despite the small conjugation space of the molecule, which consists of only 20 π electrons.

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