Synthesis and Emission Behavior of 1,3-diarylisobenzofuran-5,6-dicarboximides and Their Transformation into Naphthalene-2,3:6,7-bis(dicarboximide)s
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
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 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.
Y. Maruoka, “Photoreactions of cyclic imides. Examples of synthetic organic photochemistry”, Acc. Chem. Res. 1978, 11, 407–413.
A. Demeter, L. Biczók, T. Bérces, V. Wintgens, P. Valat, and J. Kossanyi, “Laser photolysis studies of transient processes in the photoreduction of naphthalimides by aliphatic amines”, J. Phys. Chem. 1993, 97, 3217–3224.
K. Maruyama, and Y. Kubo, “Photochemistry of phthalimides with olefins. Solvent-incorporated addition vs. cycloaddtion to imide C(=O)–N bond accompanying ring enlargement”, J. Org. Chem. 1985, 50, 1426–1435.
Y. Kubo, and M. Suto, T. Arai, P. H. Mazzocchi, L. Klingler, D. Shook, and C. Somich, “Photochemical reactions of N-methylnaphthalene-2,3-dicarboximides with alkenes”, J. Org. Chem. 1986, 51, 4404–4411.
P. Valat, V. Wintgens, J. Kossanyi, L. Biczók, A. Demeter, and T. Bérces, “ Influence of geometry on the emitting properties of 2,3-naphthalimides”, J. Am. Chem. Soc. 1992, 114, 946–953.
A. Demeter, T. Bérces, L. Biczók, V. Wintgens, P. Valat, and J. Kossanyi, “Comprehensive model of the photophysics of N-phenylnaphthalimides: The role of solvent and rotational relaxation”, J. Phys. Chem. 1996, 100, 2001–2011.
J. C. Netto-Ferreira, V. Wintgens, L. F. V. Ferreira, A. R. Garcia, L. M. Ilharco, and M. J. Lemos, “Solid complexes between N-(para-alkylphenyl)-2,3-naphthalimides and -cyclodextrin: Characterization by diffuse reflectance infrared Fourier transform spectroscopy and laser induced luminescence studies”, J. Photochem. Photobiol. A: Chem. 2000, 132, 209–217.
P. Valat, V. Wintgens, J. Kossanyi, L. Biczók, A. Demeter, and T. Bérces, “Temperature-dependent behavior of the dual fluorescence of 2-(3-fluorophenyl)-2,3-dihydro-1H-benzo[f]isoindole-1,3-dione”, Helv. Chim. Acta 2001, 84, 2813–2832.
P. Nandhikonda and M. D. Heagy, “Dual fluorescent N-aryl-2,3-naphthalimides: Applications in ratiometric DNA detection and white organic light-emitting devices”, Org. Lett. 2010, 12, 4796.
M. Oda, T. Nakamura, M. Neha, D. Miyawaki, A. Ohta, S. Kuroda, and Ryuta Miyatake “A short-step synthesis of 1,6-methanoannulene-3,4-dicarboximides and their benzene-, naphthalene-, and thiophene-annulated compounds”, Eur. J. Org. Chem. 2014, 5976–5985.
Y. Zhong, B. Kumar, S. Oh, M. T. Trinh, Y. Wu, K. Elbert, P. Li, X. Zhu, S. Xiao, F. Ng, M. L. Steigerwald, and C. Nuckolls, “Helical ribbons for molecular electronics”, J. Am. Chem. Soc. 2014, 136, 8122–8130.
X. Zhan, A. Facchetti, S. Barlow, T. J. Marks, M. A. Ratner, M. R. Wasielewski, and S. R. Marder, “Rylene and related diimides for organic electronics”, Adv. Mater. 2011, 23, 268–284.
S. Guha, F. S. Goodson, L. J. Corson, and S. Saha, “Boundaries of anion/naphthalenediimide interactions; From anion- interactions to anion-induced charge-transfer and electron-transfer phenomena”, J. Am. Chem. Soc. 2012, 134, 13679–13691.
H. Cao, V. Chang, R. Hernandez, and M. D. Heagy, “Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives”, J. Org. Chem. 2005, 71, 4929–4934.
K. Imaizumi, H. Terasima, K. Akasaka, and H. Ohrui, “Highly potent chiral labeling reagents for the discrimination of chiral alcohols”, Anal. Sci. 2003, 19, 1243–1249.
L. Kürti and B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, pp182–184, Elsevier Academic Press, Amsterdat, 2005.
M. Sato, S. Ebine, and S. Akahori, “Condensation of halobenzenes and haloferroces with phthalimide in the presence of copper (I) oxide; A simplified Gabriel reaction”, Synthesis 1982, 472–473.
S. Kuroda, N. Tamura, R. Miyatake, N. Matsumoto, Y. Horino, D. Miyawaki and M. Oda, “Synthesis and emission properties of 1,6-methanoannulene-3,4-dicarboximides, Heterocycles 2011, 83, 789–796.
M. P. Cava and P. L. Shirley, “Condensed cyclobutane aromatic compounds. X. Naphtho[b]cyclobutene”, J. Am. Chem. Soc. 1960, 82, 654–656.
T. Iwanaga, R. Tanaka, and S. Toyota, “Introduction of an arylethynyl group onto an anthracene bisimide core for molecular design of new π-conjugated compounds”, Chem. Lett. 2014, 43, 105–107.
Y. Nishina, T. Kida, and T. Ureshino, “Facile Sc(OTf)3-catalyzed generation and successive aromatization of isobenzofuran from o-dicarbonylbenzenes”, Org. Lett. 2011, 13, 3960–3963.
C. R. Hickenboth, J. S. Moore, S. R. White, N. R. Scott, J. Baudry, and S. R Wilson, “Biasing reaction pathways with mechanical force”, Nature 2007, 446, 423-427.
M. J. Haddadin, B. J. Agha, and R. F. Tabri, “Syntheses of some furans and naphtha [2,3-c] derivatives of furan, pyrrole, and thiophene”, J. Org. Chem. 1979, 44, 494–497.
M. Oda, H. Shimosasa, Y. Kumai, A. Ohta, and R. Miyatake, “An improved synthesis of arenedicarboximides by phosphine-assisted annulation of arene-1,2-dicarbaldehyde with N-substituted maleimide”, Modern Chem. 2014, 2(4), 29–35.
J. Wang, R. Zhou, Z.-R. He, and Z. He, “Phosphane-mediated domino synthesis of tetrasubstituted furans from simple terminal activated olefins”, Eur. J. Org. Chem. 2012, 6033–604.
TD-DFT calculations for the simplified derivative with a hydrogen atom at the imide nitrogen instead of a phenyl group of 6a were carried out by with the Gaussian 03 program, Revision C.01 program, Gaussian, Inc.: Pittsburgh, PA, 2003. The result is as follows: For 1st excited state, calculated wavelength is 464 nm (2.6721 eV), its oscillator strength f is 0.2561, and the description is HOMO->LUMO (0.62998). For 2nd excited state, calculated wavelength is 404 nm (3.0637 eV), its oscillator strength f is 0.2641, and the description is HOMO->LUMO +1(0.65562).
X.-F. Zhang and X. Li, “The photostability and fluorescence properties of diphenylisobenzofuran’’, J. Lumines. 2011, 131, 2263–2266.
J. Jacq, S. Tsekhanovich, M. Orio, C. Einhorn, J. Einhorn, B. Bessières, J. Chauvin, D. Jouvenot, and F. Loiseau, “Structure and dynamics of the excited states of 1,3-diarylisobenzofurans: An experimental and theoretical study”, Photochem. & Photobio. 2012, 88, 633-638.
D.-T. Hsu and C.-H. Lin, “Synthesis of benzo[c] and naphtho[c]heterocycle diesters and dinitriles via homoelongation,” J. Org. Chem. 2009, 74, 9180–9187.
M. P. Cava, A. A. Deana, K. Muth, and m. J. Mitchell, Org. Synth. 1973, Coll. Vol. 5, 944–945.
W. R. Roderick, “The isomerism of N-substituted maleimide,” J. Am. Chem. Soc. 1957, 79, 1710–1712.
H. Firouzabadi, D. Mohajer, and M. Entezari-Moghadam, “Barium ferrate monohydrate BaFeO4•H2O, a useful oxidant for the oxidation of organic compounds under aprotic conditions”, Bull. Chem. Soc. Jp. 1988, 61(6), 2185–2189.