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

Haruki Shimosasa; Ryuta Miyatake; Naoki Kobayashi; Mitsunori Oda

doi:doi:10.11648/j.mc.20160402.11

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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

Haruki Shimosasa, Ryuta Miyatake, Naoki Kobayashi, Mitsunori Oda

Published in Modern Chemistry (Volume 4, Issue 2)

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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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
SP  - 16
EP  - 23
PB  - Science Publishing Group
SN  - 2329-180X
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

Haruki Shimosasa

Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan
Ryuta Miyatake

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

Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan
Mitsunori Oda

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

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Plain Text BibTeX RIS

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

Copy | Download

@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}
}

Copy | Download

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
SP  - 16
EP  - 23
PB  - Science Publishing Group
SN  - 2329-180X
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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