Synthesis and Physical Properties of Novel 7, 12-Diaryl-N-phenylbenzo[k]fluoranthene-9, 10-dicarbox- imides
Modern Chemistry
Volume 4, Issue 6, December 2016, Pages: 52-58
Received: Dec. 14, 2016; Accepted: Dec. 22, 2016; Published: Jan. 16, 2017
Views 3083      Downloads 82
Authors
Yuki Nakahara, Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, Japan
Haruki Shimosasa, Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, 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, Matsumoto, Japan
Mitsunori Oda, Department of Chemistry, Faculty of Science, Shinshu University, Matsumoto, Japan
Article Tools
Follow on us
Abstract
The title arene-dicarboximides 8a–8d, having a benzo[k]fluoranthene skeleton, were synthesized in two steps from N-phenyl-1, 3-diarylisobenzofuran-5, 6-dicarboximides 4a–4d by the Diels-Alder reaction with acenaphthylene and subsequent dehydration with trifluoromethanesulfonic acid. Under photo-excitation these dicarboximides emit blue light, notably, with high quantum yields.
Keywords
Isobenzofuran-Dicarboximides, Diels-Alder Reaction, Dehydration, Triflic Acid, Fluorescence
To cite this article
Yuki Nakahara, Haruki Shimosasa, Ryuta Miyatake, Naoki Kobayashi, Mitsunori Oda, Synthesis and Physical Properties of Novel 7, 12-Diaryl-N-phenylbenzo[k]fluoranthene-9, 10-dicarbox- imides, Modern Chemistry. Vol. 4, No. 6, 2016, pp. 52-58. doi: 10.11648/j.mc.20160406.11
Copyright
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.
References
[1]
Y.-Y. Li, H.-Y. Lu, M. Li, X.-J. Li, and C.-F. Chen, “Dihydroindeno [2, 1-c]fluorene-based imide dyes: Synthesis, structures, photophysical and electrochemical properties”, J. Org. Chem. 2014, 79, 2139–2147.
[2]
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.
[3]
D. Xia, T. Marszalek, M. Li, X. Guo, M. Baumgarten, W. Pisula, and K. Müllen, “Solution-processable n-type organic semiconductors based on angular-shaped 1-(12H-dibenzofluoren-12-ylidene) malononitrilediimide”, Org. Lett. 2015, 17, 3074–3077.
[4]
B. Yao, X. Ye, J. Zhang, and X. Wan, “Electrochromism of a fused acceptor-donor-acceptor triad covering entire UV-vis and near-infrared regions”, Org. Lett. 2014, 16, 5378–5381.
[5]
C. Yuan, S. Saito, C. Camacho, S. Irle, I. Hisaki, and S. Yamaguchi, “A -conjugated system with flexibility and rigidity that shows environment-dependent RGB luminescence”, J. Am. Chem. Soc. 2013, 135, 8842–8845.
[6]
T. V. Pho, F. M. Toma, M. L. Chabinyc, and F. Wudl, “Self-assembling decacyclene triimides prepared through a regioselective hextuple Friedel-Crafts carbamylation”, Angew. Chem. Int. Ed. 2013, 52, 1446–1451.
[7]
S. Seifert, K. Shoyama, D. Schmidt, and F. Würthner, “An electron-poor C64 nanographene by palladium-catalyzed cascade C–C bond formation: One-pot synthesis and single-crystal structure analysis”, Angew. Chem. Int. Ed. 2016, 55, 6390–6395.
[8]
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.
[9]
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, 4796–4799.
[10]
P. Nandhikonda and M. D. Heagy, “An abiotic fluorescent probe for cardiac troponin I”, J. Am. Chem. Soc. 2011, 133, 14972–14974.
[11]
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.
[12]
I. Saito, M. Takayama, and S. Kawanishi, “Photoactivatable DNA-cleaving amino acids: Highly sequence-selective DNA photocleavage by novel L-lysine derivatives”, J. Am. Chem. Soc. 1995, 117, 5590–5591.
[13]
I. Saito, M. Takayama, H. Sugiyama, K. Nakatani, A. Tsuchida, and M. Yamamoto, “Photoinduced DNA cleavage via electron transfer: Demonstration that guanine residues located 5’ to guanine are the most electron-donating sites”, J. Am. Chem. Soc. 1995, 117, 6406–6407.
[14]
S. Li, L. Zhou, Z. Song, F. Bao, K. Kanno, and T. Takahashi, “Effect of substituents at 1, 4-positions of polycyclic aromatic compounds and preparation of 2, 3-difunctionalized pentacenes and naphthacenes”, Heterocycles 2007, 73, 519–536.
[15]
V. Nair and K. G. Abhilash, “Engaging Morita-Baylis-Hillman reaction for the generation of isobenzofuran and the consequent entry into highly substituted aromatic systems”, Synthesis 2005, 1967–1970.
[16]
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.
[17]
T. Iwanaga, R. Tanaka, and S. Toyota, “Introduction of an arylethynyl group onto an anthracene bisimide core for molecular design of new -conjugated compounds”, Chem. Lett. 2014, 43, 105–107.
[18]
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, 29–35.
[19]
H. Shimosasa, R. Miyatake, N. Kobayashi, and M. 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 Chem. 2016, 4, 16–23.
[20]
N. Kobayashi, S. Yamamoto, H. Shimosasa, M. Oda, and R. Miyatake, “Convenient synthesis of benzo [b]thiophene-5, 6-dicarboximide derivatives and their photophysical properties”, Modern Chem. 2016, 4, 45–51.
[21]
T. Yanagisawa, N. Kabayashi, H. Shimosasa, Y. Kumai, R. Miytake, and M. Oda, “Synthesis and fluorescence property of, 2, 3-naphthalimide derivatives bearing phenyl substituents on the naphthalene skeleton”, Dyes Pigments 2017, 136, 859–864.
[22]
M. J. Haddadin, B. J. Agha, and R. F. Tabri, “Syntheses of some furans and naphtho [2, 3-c] derivatives of furan, pyrrole, and thiophene”, J. Org. Chem. 1979, 44, 494–497.
[23]
N. C. Thanh, M. Ikai, T. Kajioka, H. Fujikawa, Y. Taga, Y. Zhang, S. Ogawa, H. Shimada, Y. Miyahara, S. Kuroda, and M. Oda, “Synthesis of N, N, N’, N’-tetrasubstituted 1, 3-bis (4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices”, Tetrahedron 2006, 62, 11227–11239.
[24]
A. J. Mancuso and D. Swern, “Activated dimethyl sulfoxide: Useful reagents for synthesis”, Synthesis 1981, 165–185.
[25]
The structures were optimized at the B3LYP/6-31G (d) level of theory. DFT calculations were carried out by with the Gaussian 03 program, Revision D.01 program, Gaussian, Inc.: Pittsburgh, PA, 2003.
[26]
Y.-H. Kung, Y.-S. Cheng, C.-C. Tai, W.-S. Liu, C.-C. Shin, C.-C. Ma, Y.-C. Tsai, T.-C. Wu, M.-Y. Kuo, and Y.-T, Wu, “Synthesis, structures, and physical properties of benzo [k]fluoranthene-based linear acenes”, Chem. Eur. J. 2010, 16, 5909–5919.
[27]
W. R. Dawson and M. W. Windsor, “Fluorescence yields of aromatic compounds”, J. Phys. Chem. 1968, 72, 3251–3260.
[28]
W. H. Melhuish, “Quantum efficiencies of fluorescence organic substances: Effect of solvent and concentration of the fluorescent solute”, J. Phys. Chem. 1961, 65, 229–235.
[29]
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, 6033–6041.
[30]
Because of low solubility of this compound in deuterated solvents, its satisfactory 13C NMR spectrum was not obtained.
ADDRESS
Science Publishing Group
1 Rockefeller Plaza,
10th and 11th Floors,
New York, NY 10020
U.S.A.
Tel: (001)347-983-5186