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Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s

Received: 10 March 2016     Accepted: 18 March 2016     Published: 6 April 2016
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Abstract

Phosphine-assisted annulation of 2,5-diarylfuran-3,4-dicarbaldehydes with maleimides provided the title isobenzofurans in satisfactory yields. An effect of the substituents at the para position of the aryl groups in these isobenzofurans was demonstrated clearly by a red shift in their UV-vis absorption and emission spectra. They were transformed into the corresponding naphthalene-2,3:6,7-bis(dicarboximide)s by Diels-Alder reaction with another maleimide and subsequent dehydration with the aid of trifluoromethanesulfonic acid. Emission behavior of the title bis(dicarboximide)s is also described.

Published in Modern Chemistry (Volume 4, Issue 2)
DOI 10.11648/j.mc.20160402.11
Page(s) 16-23
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2016. Published by Science Publishing Group

Keywords

Isobenzofuran, Naphthalene-bis(dicarboximide)s, Furan-3,4-dicarbaldehydes, Substituent Effect, Dehydration, Diels-Alder Reaction

References
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  • APA Style

    Haruki Shimosasa, Ryuta Miyatake, Naoki Kobayashi, Mitsunori Oda. (2016). Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s. Modern Chemistry, 4(2), 16-23. https://doi.org/10.11648/j.mc.20160402.11

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    ACS Style

    Haruki Shimosasa; Ryuta Miyatake; Naoki Kobayashi; Mitsunori Oda. Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s. Mod. Chem. 2016, 4(2), 16-23. doi: 10.11648/j.mc.20160402.11

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    AMA Style

    Haruki Shimosasa, Ryuta Miyatake, Naoki Kobayashi, Mitsunori Oda. Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s. Mod Chem. 2016;4(2):16-23. doi: 10.11648/j.mc.20160402.11

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  • @article{10.11648/j.mc.20160402.11,
      author = {Haruki Shimosasa and Ryuta Miyatake and Naoki Kobayashi and Mitsunori Oda},
      title = {Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s},
      journal = {Modern Chemistry},
      volume = {4},
      number = {2},
      pages = {16-23},
      doi = {10.11648/j.mc.20160402.11},
      url = {https://doi.org/10.11648/j.mc.20160402.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20160402.11},
      abstract = {Phosphine-assisted annulation of 2,5-diarylfuran-3,4-dicarbaldehydes with maleimides provided the title isobenzofurans in satisfactory yields. An effect of the substituents at the para position of the aryl groups in these isobenzofurans was demonstrated clearly by a red shift in their UV-vis absorption and emission spectra. They were transformed into the corresponding naphthalene-2,3:6,7-bis(dicarboximide)s by Diels-Alder reaction with another maleimide and subsequent dehydration with the aid of trifluoromethanesulfonic acid. Emission behavior of the title bis(dicarboximide)s is also described.},
     year = {2016}
    }
    

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  • TY  - JOUR
    T1  - Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s
    AU  - Haruki Shimosasa
    AU  - Ryuta Miyatake
    AU  - Naoki Kobayashi
    AU  - Mitsunori Oda
    Y1  - 2016/04/06
    PY  - 2016
    N1  - https://doi.org/10.11648/j.mc.20160402.11
    DO  - 10.11648/j.mc.20160402.11
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
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    EP  - 23
    PB  - Science Publishing Group
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    UR  - https://doi.org/10.11648/j.mc.20160402.11
    AB  - Phosphine-assisted annulation of 2,5-diarylfuran-3,4-dicarbaldehydes with maleimides provided the title isobenzofurans in satisfactory yields. An effect of the substituents at the para position of the aryl groups in these isobenzofurans was demonstrated clearly by a red shift in their UV-vis absorption and emission spectra. They were transformed into the corresponding naphthalene-2,3:6,7-bis(dicarboximide)s by Diels-Alder reaction with another maleimide and subsequent dehydration with the aid of trifluoromethanesulfonic acid. Emission behavior of the title bis(dicarboximide)s is also described.
    VL  - 4
    IS  - 2
    ER  - 

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Author Information
  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

  • Centre for Environmental Conservation and Research Safety, University of Toyama, Toyama, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

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