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Katayama T, Nakatsuka S, Hirai H, et al. Two-Step Synthesis of Boron-Fused Double Helicenes. J Am Chem Soc. 2016;138(16):5210-3doi: 10.1021/jacs.6b01674.
Katayama, T., Nakatsuka, S., Hirai, H., Yasuda, N., Kumar, J., Kawai, T., & Hatakeyama, T. (2016). Two-Step Synthesis of Boron-Fused Double Helicenes. Journal of the American Chemical Society, 138(16), 5210-3. https://doi.org/10.1021/jacs.6b01674
Katayama, Takazumi, et al. "Two-Step Synthesis of Boron-Fused Double Helicenes." Journal of the American Chemical Society vol. 138,16 (2016): 5210-3. doi: https://doi.org/10.1021/jacs.6b01674
Katayama T, Nakatsuka S, Hirai H, Yasuda N, Kumar J, Kawai T, Hatakeyama T. Two-Step Synthesis of Boron-Fused Double Helicenes. J Am Chem Soc. 2016 Apr 27;138(16):5210-3. doi: 10.1021/jacs.6b01674. Epub 2016 Apr 14. PMID: 27077723.
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J Am Chem Soc. 2016 Apr 27;138(16):5210-3. doi: 10.1021/jacs.6b01674. Epub 2016 Apr 14.

Two-Step Synthesis of Boron-Fused Double Helicenes.

Journal of the American Chemical Society

Takazumi Katayama, Soichiro Nakatsuka, Hiroki Hirai, Nobuhiro Yasuda, Jatish Kumar, Tsuyoshi Kawai, Takuji Hatakeyama

Affiliations

  1. Department of Chemistry, School of Science and Technology, Kwansei Gakuin University , 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
  2. Japan Synchrotron Radiation Research Institute (JASRI)/SPring-8 , 1-1-1, Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan.
  3. Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayama, Ikoma, Nara 630-0192, Japan.
  4. Elements Strategy Initiative for Catalysts and Batteries, Kyoto University , Katsura, Kyoto 615-8520, Japan.

PMID: 27077723 DOI: 10.1021/jacs.6b01674

Abstract

Novel boron-fused double [5]helicenes were synthesized from hexabromobenzene in two steps via Hart reaction and demethylative cyclization. The parent helicene shows excellent ambipolar conductivity, which can be explained by unique 3D π-stacking with a brickwork arrangement. Moreover, the introduction of four tert-butyl groups suppresses racemization, enabling optical resolution. The enantiomerically pure helicene shows deep blue fluorescence with Commission Internationale de l'Eclairage coordinates of (0.15, 0.08) and circularly polarized luminescence activity.

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