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
Volume 4, Issue 2, April 2016, Pages: 16-23
Received: Mar. 10, 2016; Accepted: Mar. 18, 2016; Published: Apr. 6, 2016
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Authors
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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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.
Keywords
Isobenzofuran, Naphthalene-bis(dicarboximide)s, Furan-3,4-dicarbaldehydes, Substituent Effect, Dehydration, Diels-Alder Reaction
To cite this article
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, Modern Chemistry. Vol. 4, No. 2, 2016, pp. 16-23. doi: 10.11648/j.mc.20160402.11
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Copyright © 2016 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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