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