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

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.

Synthesis and Physical Properties of Novel 7, 12-Diaryl-<i>N</i>-phenylbenzo[<i>k</i>]fluoranthene-9, 10-dicarbox- imides

“…In this study we employed four different 1, 3-diaryl-N-phenylisobenzofuran-5, 6-dicarboximides 4a-d as a diene part in the Diels-Alder reaction. We have already reported the synthesis of 4a-c. [19] The new biphenyl-substituted derivative 4d was synthesized in four steps from dimethyl 2, 5-bis (4-bromophenyl)furan-3, 4-dicarboxylate (9) according to Fig. 3.…”

“…[9][10] These findings have prompted organic chemists to develop various new synthetic methods access to dicarboximide compounds. [14][15][16][17] We recently developed an efficient annulation between arene-1, 2-dicarbaldehydes and maleimides [18][19][20][21] by improving the previously reported Haddadin's result. [22] As shown in Fig.…”

“…We also reported that isobenzofuran-dicarboximides 4 served as a diene part in Diels-Alder reaction and naphthalene- Bis(dicarboximide)s 6 could be obtained by dehydration of the Diels-Alder adducts with various Brønsted acids. [19] During a course of our study on development of synthetic methods for a variety of arene-dicarboximides, we have further pursued cycloaddition reactions of 4. In this paper, we describe transformation from 4a-4d into the title compounds 8a-8d by its Diels-Alder reaction with acenaphthylene (7) and subsequent dehydration with trifluoromethanesulfonic acid (triflic acid).…”

Convenient Synthesis of Benzo[<i>b</i>]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties

“…[5][6] Thus, synthetic improvements to access to these imides have continuously made. [7][8] We recently developed an efficient method of annulation between arene-1,2-dicarbaldehydes and maleimides [9][10][11] by improving the previously reported Haddadin's result. [12] various naphthalene-, anthracene-, and isobenzofuran-dicarboximides 2-4 can be obtained in one-pot from the corresponding arene-1,2-dicarbaldehydes and maleimides in good to high yields (Fig.…”