Abstract
The reaction of the free amine group in polyaryl-substituted imidazole structures with phenyl isocyanate or dimethyl acetylenedicarboxylate gave two new series of polyaryl-substituted imidazoles: biaryl ureas or vinyl esters, respectively. Besides their spectroscopic analysis, we explored the optical and electrochemical properties of these highly conjugated scaffolds. Comparing these properties in two categories of products yielded interesting results.
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T.M. Figueira-Duarte, K. Mullen, Chem. Rev. 11, 7260 (2011)
E. Holder, B.M.W. Langeveld, U.S. Schubert, Adv. Mater. 17, 1109 (2005)
J.H. Burroughes, D.D. Bradley, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, P.L. Burns, A.B. Holmes, Nature 347(6293), 539 (1990)
M.D. McGehee, A.J. Heeger, Adv. Mater. 12, 1655 (2000)
A.R. Murphy, J.M.J. Frechet, Chem. Rev. 107, 1066 (2007)
B. Crone, A. Dodabalapur, A. Gelperin, L. Torsi, H.E. Katz, A.J. Lovinger, Z. Bao, Appl. Phys. Lett. 78, 2229 (2001)
T. Someya, H.E. Katz, A. Gelperin, A.J. Lovinger, A. Dodabalapur, Appl. Phys. Lett. 81, 3079 (2002)
T. Kowada, J. Kituta, A. Kubo, M. Ishii, H. Maeda, S. Mizukami, K. Kikuchi, J. Am. Chem. Soc. 133, 17772 (2011)
S. Yao, H.Y. Ahn, X.H. Wang, J. Fu, E.W.V. Stryland, D.J. Hagan, K.D. Belfield, J. Org. Chem. 75, 3965 (2010)
N. Fu, Y.J. Xiong, T.C. Squier, J. Am. Chem. Soc. 134, 18530 (2012)
Y.L. Wang, T.L. Liu, L.Y. Bu, J.F. Li, C. Yang, X.J. Li, Y. Tao, W.J. Yang, J. Phys. Chem. 116, 15576 (2012)
Y.J. Cheng, J.D. Luo, S. Hau, D.H. Bale, T.D. Kim, Z.W. Shi, D.B. Lao, N.M. Tucker, Y.Q. Tian, L.R. Dalton, P.J. Reid, A.K.Y. Jen, Chem. Mater. 19, 1154 (2007)
D.J. Armitt, G.T. Crisp, J. Org. Chem. 71, 3417 (2006)
H. Jin, X. Li, T. Tan, S. Wang, Y. Xiao, J. Tian, Dyes Pigments 106, 154 (2014)
R.E. Martin, F. Diederich, Angew. Chem. Int. Ed. 38, 1350 (1999)
J.L. Segura, N. Martín, J. Mater. Chem. 10, 2403 (2000)
J. Kulhánek, F. Bureš, Beilstein J. Org. Chem. 8, 25 (2012)
Z.-P. Chen, H.-B. Wang, Y.-Q. Wang, Q.-H. Zhu, Y. Xie, S.-W. Liu, Tetrahedron 29, 4379 (2014)
G. Choudhary, R.K. Peddinti, Green Chem. 13, 3290 (2011)
M. Lashkari, M.T. Maghsoodlou, M. Karima, M. Kangani, J. Chil. Chem. Soc. 63, 3799 (2018)
J. Liu, W. Wei, T. Zhao, X. Liu, J. Wu, W. Yu, J. Chang, J. Org. Chem. 81, 9326 (2016)
W. Liu, L. Tan, P. Zhou, C. Chen, Q. Zhang, Synlett 24, 991 (2013)
J. Pan, X. Li, F. Lin, J. Liu, N. Jiao, Chem 6, 1427 (2018)
Y. Wang, C.-M. Jiang, H.-L. Li, F.-S. He, X. Luo, W.-P. Deng, J. Org. Chem. 81, 8653 (2016)
F. Huang, P. Wu, L. Wang, J. Chen, C. Sun, Z. Yu, J. Org. Chem. 79, 10553 (2014)
R. Sharma, R.A. Vishwakarma, S.B. Bharate, Adv. Synth. Catal. 358, 3027 (2016)
C. Zheng, Y. Wang, R. Fan, Org. Lett. 17, 916 (2015)
X. Duan, X. Kong, X. Zhao, K. Yang, H. Zhou, D. Zhou, Y. Zhang, J. Liu, J. Ma, N. Liu, Z. Wang, Tetrahedron Lett. 57, 1446 (2016)
F.D. Lewis, T.L. Kurth, W. Liu, Photochem. Photobiol. Sci. 1, 30 (2002)
J.K. Dannecker, H. Rust, Cryst. Struct. Commun. 8, 429 (1979)
M.C. Etter, T.W. Panunto, J. Am. Chem. Soc. 110, 5896 (1988)
P. Ganis, G. Avitabile, E. Benedetti, C. Pedone, M. Goodman, Proc. Natl. Acad. Sci. U. S. A. 67, 426 (1970)
H. Kagechika, I. Azumaya, K. Yamaguchi, K. Shudo, Chem. Pharm. Bull. 44, 460 (1996)
K. Mori, A. Kanie, Y. Horiguchi, K. Isobe, Heterocycles 51, 2377 (1999)
R.R. Schmidt, J. Kast, H. Speer, Synthesis 9, 725 (1983)
A.Z. Halimehjani, M.R. Saidi, Tetrahedron Lett. 49, 1244 (2008)
N.D. Heindel, I.S. Bechara, P.D. Kennewell, J. Molnar et al., J. Org. Chem. 11, 1218 (1968)
D. Zewge, C. Chen, C. Deer, P.G. Dormer, D.L. Hughes, J. Org. Chem. 72, 4276 (2007)
R. Hosseinzadeh, Y. Sarrafi, M. Mohadjerani, F. Mohammadpourmir, Tetrahedron Lett. 49, 840 (2008)
R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, H. Mehdinejad, Synlett 9, 1517 (2004)
R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, M. Alikarami, Synlett 7, 1101 (2005)
R. Hosseinzadeh, M. Tajbakhsh, M. Alikarami, Tetrahedron Lett. 47, 5203 (2006)
A.G. Sergeev, G.A. Artamkina, I.P. Beletskaya, Tetrahedron Lett. 44, 4719 (2003)
S.N. Gavade, R.S. Balaskar, M.S. Mane, P.N. Pabrekar, M.S. Shingare, D.V. Mane, Chin. Chem. Lett. 22, 292 (2011)
R. Hosseinzadeh, Y. Sarrafi, N. Aghili, Chin. Chem. Lett. 21, 1171 (2010)
A.A. Fakhree, Z. Ghasemi, A. Shahrisa, H. Mostafavi, ChemistrySelect 4, 2959 (2019)
Z. Ghasemi, A. Mirzaie, R. Arabzadeh, Z. Fathi, A. Abolghassemi Fakhree, J. Chem. Res. 43, 262 (2019)
Z. Ghasemi, Z. Fathi, Res. Chem. Intermediates. 43, 3131 (2017)
Z. Ghasemi, Z. Zakeri, M. Allahvirdinesbat, Turk. J. Chem. 40, 729 (2016)
H. Kessler, H. Oschkinat, C. Griesinger, W.J.J. Bermel, Magn. Reson. 70, 106 (1986)
J. Stonehouse, P. Adell, J. Keeler, A.J. Shaka, J. Am. Chem. Soc. 116, 6037 (1994)
K. Stott, J. Stonehouse, J. Keeler, T.L. Hwang, A.J. Shaka, J. Am. Chem. Soc. 117, 4199 (1995)
R. Hülnhagen, H. Baumgärtel, J. Electroanal. Chem. 98, 119 (1979)
K. Pekmez, H. Özyöruk, A. Yildiz, Ber. Bunsenges. Phys. Chem. 96, 1805 (1992)
T. Sakamoto, T. Nagano, Y. Kondo, H. Yamanaka, Synthesis 3, 215 (1990)
Y. Iwanami, Bull. Chem. Soc. Jpn. 44, 1311 (1971)
S.K. Khetan, J.G. Hiriyakkanavar, M.V. George, Tetrahedron 24, 1567 (1968)
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Authors thank the research affairs of the University of Tabriz for their financial support.
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Fakhree, A.A., Mohammadzadeh, R., Alipour, E. et al. Synthesis of new polyaryl-substituted imidazoles bridged on enamine or urea moieties and evaluation of their optical and electrochemical properties. Res Chem Intermed 46, 2069–2082 (2020). https://doi.org/10.1007/s11164-020-04078-y
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DOI: https://doi.org/10.1007/s11164-020-04078-y