Improved Synthesis of Bay‐Monobrominated Perylene Diimides

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  • Keisuke Fujimoto
    Department of Applied Chemistry Faculty of Engineering Shizuoka University 3-5-1 Johoku, Naka-ku Hamamatsu 432-8561 Japan
  • Kentaro Uchida
    Department of Applied Chemistry Faculty of Engineering Shizuoka University 3-5-1 Johoku, Naka-ku Hamamatsu 432-8561 Japan
  • Mayuko Nakamura
    Department of Applied Chemistry Faculty of Engineering Shizuoka University 3-5-1 Johoku, Naka-ku Hamamatsu 432-8561 Japan
  • Toshiyasu Inuzuka
    Division of Instrumental Analysis Life Science Research Center Gifu University 1-1 Yanagido Gifu 501-1193 Japan
  • Naohiro Uemura
    Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University 1-33 Yayoi-cho, Inage-ku Chiba 263-8522 Japan
  • Masami Sakamoto
    Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University 1-33 Yayoi-cho, Inage-ku Chiba 263-8522 Japan
  • Masaki Takahashi
    Department of Applied Chemistry Faculty of Engineering Shizuoka University 3-5-1 Johoku, Naka-ku Hamamatsu 432-8561 Japan

書誌事項

公開日
2020-12-17
資源種別
journal article
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/slct.202004432
公開者
Wiley

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説明

<jats:title>Abstract</jats:title> <jats:p> The work presents the development of practical synthetic methods toward bay‐monobrominated perylene diimides (PDIs) that have been regarded as important synthetic intermediates for the fabrication of new photonic, optoelectronic, and photovoltaic materials. In the case of PDIs with long branched <jats:italic>N</jats:italic> ‐alkyl solubilizers, bromination using <jats:italic>N</jats:italic> ‐bromosuccinimide (NBS) and FeCl <jats:sub>3</jats:sub> successfully provided the corresponding monobromides. This protocol improved the reaction outcomes in terms of product yield and operational easiness, superior to the conventional ones with liquid bromine. Alternatively, imidation of the corresponding dianhydride, easily prepared through monobromination of perylene‐3,4,9,10‐tetrabenzyl ester (PTE), recorded high efficiency for generation of PDI monobromides without solubilizing <jats:italic>N</jats:italic> ‐substituents. This complementary method made it possible to access a series of new PDI monobromides which had been unobtainable through existing methods. </jats:p>

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