Advertisement

Synthesis of new polyaryl-substituted imidazoles bridged on enamine or urea moieties and evaluation of their optical and electrochemical properties

  • Ameneh Abolghassemi Fakhree
  • Roghayeh Mohammadzadeh
  • Esmaeel Alipour
  • Zarrin GhasemiEmail author
Article
  • 28 Downloads

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.

Graphic abstract

Keywords

Biarylureas Cyclic voltammetry Fluorescence emission Polyaryl-substituted imidazoles Vinyl esters 

Notes

Acknowledgements

Authors thank the research affairs of the University of Tabriz for their financial support.

Supplementary material

11164_2020_4078_MOESM1_ESM.docx (10.7 mb)
Supplementary material 1 (DOCX 10965 kb)

References

  1. 1.
    T.M. Figueira-Duarte, K. Mullen, Chem. Rev. 11, 7260 (2011)CrossRefGoogle Scholar
  2. 2.
    E. Holder, B.M.W. Langeveld, U.S. Schubert, Adv. Mater. 17, 1109 (2005)CrossRefGoogle Scholar
  3. 3.
    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)CrossRefGoogle Scholar
  4. 4.
    M.D. McGehee, A.J. Heeger, Adv. Mater. 12, 1655 (2000)CrossRefGoogle Scholar
  5. 5.
    A.R. Murphy, J.M.J. Frechet, Chem. Rev. 107, 1066 (2007)PubMedCrossRefPubMedCentralGoogle Scholar
  6. 6.
    B. Crone, A. Dodabalapur, A. Gelperin, L. Torsi, H.E. Katz, A.J. Lovinger, Z. Bao, Appl. Phys. Lett. 78, 2229 (2001)CrossRefGoogle Scholar
  7. 7.
    T. Someya, H.E. Katz, A. Gelperin, A.J. Lovinger, A. Dodabalapur, Appl. Phys. Lett. 81, 3079 (2002)CrossRefGoogle Scholar
  8. 8.
    T. Kowada, J. Kituta, A. Kubo, M. Ishii, H. Maeda, S. Mizukami, K. Kikuchi, J. Am. Chem. Soc. 133, 17772 (2011)PubMedCrossRefPubMedCentralGoogle Scholar
  9. 9.
    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)PubMedPubMedCentralCrossRefGoogle Scholar
  10. 10.
    N. Fu, Y.J. Xiong, T.C. Squier, J. Am. Chem. Soc. 134, 18530 (2012)PubMedCrossRefPubMedCentralGoogle Scholar
  11. 11.
    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)Google Scholar
  12. 12.
    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)CrossRefGoogle Scholar
  13. 13.
    D.J. Armitt, G.T. Crisp, J. Org. Chem. 71, 3417 (2006)PubMedCrossRefPubMedCentralGoogle Scholar
  14. 14.
    H. Jin, X. Li, T. Tan, S. Wang, Y. Xiao, J. Tian, Dyes Pigments 106, 154 (2014)CrossRefGoogle Scholar
  15. 15.
    R.E. Martin, F. Diederich, Angew. Chem. Int. Ed. 38, 1350 (1999)CrossRefGoogle Scholar
  16. 16.
    J.L. Segura, N. Martín, J. Mater. Chem. 10, 2403 (2000)CrossRefGoogle Scholar
  17. 17.
    J. Kulhánek, F. Bureš, Beilstein J. Org. Chem. 8, 25 (2012)PubMedPubMedCentralCrossRefGoogle Scholar
  18. 18.
    Z.-P. Chen, H.-B. Wang, Y.-Q. Wang, Q.-H. Zhu, Y. Xie, S.-W. Liu, Tetrahedron 29, 4379 (2014)CrossRefGoogle Scholar
  19. 19.
    G. Choudhary, R.K. Peddinti, Green Chem. 13, 3290 (2011)CrossRefGoogle Scholar
  20. 20.
    M. Lashkari, M.T. Maghsoodlou, M. Karima, M. Kangani, J. Chil. Chem. Soc. 63, 3799 (2018)CrossRefGoogle Scholar
  21. 21.
    J. Liu, W. Wei, T. Zhao, X. Liu, J. Wu, W. Yu, J. Chang, J. Org. Chem. 81, 9326 (2016)PubMedCrossRefPubMedCentralGoogle Scholar
  22. 22.
    W. Liu, L. Tan, P. Zhou, C. Chen, Q. Zhang, Synlett 24, 991 (2013)CrossRefGoogle Scholar
  23. 23.
    J. Pan, X. Li, F. Lin, J. Liu, N. Jiao, Chem 6, 1427 (2018)CrossRefGoogle Scholar
  24. 24.
    Y. Wang, C.-M. Jiang, H.-L. Li, F.-S. He, X. Luo, W.-P. Deng, J. Org. Chem. 81, 8653 (2016)PubMedCrossRefPubMedCentralGoogle Scholar
  25. 25.
    F. Huang, P. Wu, L. Wang, J. Chen, C. Sun, Z. Yu, J. Org. Chem. 79, 10553 (2014)PubMedCrossRefPubMedCentralGoogle Scholar
  26. 26.
    R. Sharma, R.A. Vishwakarma, S.B. Bharate, Adv. Synth. Catal. 358, 3027 (2016)CrossRefGoogle Scholar
  27. 27.
    C. Zheng, Y. Wang, R. Fan, Org. Lett. 17, 916 (2015)PubMedCrossRefPubMedCentralGoogle Scholar
  28. 28.
    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)CrossRefGoogle Scholar
  29. 29.
    F.D. Lewis, T.L. Kurth, W. Liu, Photochem. Photobiol. Sci. 1, 30 (2002)PubMedCrossRefPubMedCentralGoogle Scholar
  30. 30.
    J.K. Dannecker, H. Rust, Cryst. Struct. Commun. 8, 429 (1979)Google Scholar
  31. 31.
    M.C. Etter, T.W. Panunto, J. Am. Chem. Soc. 110, 5896 (1988)CrossRefGoogle Scholar
  32. 32.
    P. Ganis, G. Avitabile, E. Benedetti, C. Pedone, M. Goodman, Proc. Natl. Acad. Sci. U. S. A. 67, 426 (1970)PubMedPubMedCentralCrossRefGoogle Scholar
  33. 33.
    H. Kagechika, I. Azumaya, K. Yamaguchi, K. Shudo, Chem. Pharm. Bull. 44, 460 (1996)CrossRefGoogle Scholar
  34. 34.
    K. Mori, A. Kanie, Y. Horiguchi, K. Isobe, Heterocycles 51, 2377 (1999)CrossRefGoogle Scholar
  35. 35.
    R.R. Schmidt, J. Kast, H. Speer, Synthesis 9, 725 (1983)CrossRefGoogle Scholar
  36. 36.
    A.Z. Halimehjani, M.R. Saidi, Tetrahedron Lett. 49, 1244 (2008)CrossRefGoogle Scholar
  37. 37.
    N.D. Heindel, I.S. Bechara, P.D. Kennewell, J. Molnar et al., J. Org. Chem. 11, 1218 (1968)Google Scholar
  38. 38.
    D. Zewge, C. Chen, C. Deer, P.G. Dormer, D.L. Hughes, J. Org. Chem. 72, 4276 (2007)PubMedCrossRefGoogle Scholar
  39. 39.
    R. Hosseinzadeh, Y. Sarrafi, M. Mohadjerani, F. Mohammadpourmir, Tetrahedron Lett. 49, 840 (2008)CrossRefGoogle Scholar
  40. 40.
    R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, H. Mehdinejad, Synlett 9, 1517 (2004)CrossRefGoogle Scholar
  41. 41.
    R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, M. Alikarami, Synlett 7, 1101 (2005)CrossRefGoogle Scholar
  42. 42.
    R. Hosseinzadeh, M. Tajbakhsh, M. Alikarami, Tetrahedron Lett. 47, 5203 (2006)CrossRefGoogle Scholar
  43. 43.
    A.G. Sergeev, G.A. Artamkina, I.P. Beletskaya, Tetrahedron Lett. 44, 4719 (2003)CrossRefGoogle Scholar
  44. 44.
    S.N. Gavade, R.S. Balaskar, M.S. Mane, P.N. Pabrekar, M.S. Shingare, D.V. Mane, Chin. Chem. Lett. 22, 292 (2011)CrossRefGoogle Scholar
  45. 45.
    R. Hosseinzadeh, Y. Sarrafi, N. Aghili, Chin. Chem. Lett. 21, 1171 (2010)CrossRefGoogle Scholar
  46. 46.
    A.A. Fakhree, Z. Ghasemi, A. Shahrisa, H. Mostafavi, ChemistrySelect 4, 2959 (2019)CrossRefGoogle Scholar
  47. 47.
    Z. Ghasemi, A. Mirzaie, R. Arabzadeh, Z. Fathi, A. Abolghassemi Fakhree, J. Chem. Res. 43, 262 (2019)CrossRefGoogle Scholar
  48. 48.
    Z. Ghasemi, Z. Fathi, Res. Chem. Intermediates. 43, 3131 (2017)CrossRefGoogle Scholar
  49. 49.
    Z. Ghasemi, Z. Zakeri, M. Allahvirdinesbat, Turk. J. Chem. 40, 729 (2016)CrossRefGoogle Scholar
  50. 50.
    H. Kessler, H. Oschkinat, C. Griesinger, W.J.J. Bermel, Magn. Reson. 70, 106 (1986)Google Scholar
  51. 51.
    J. Stonehouse, P. Adell, J. Keeler, A.J. Shaka, J. Am. Chem. Soc. 116, 6037 (1994)CrossRefGoogle Scholar
  52. 52.
    K. Stott, J. Stonehouse, J. Keeler, T.L. Hwang, A.J. Shaka, J. Am. Chem. Soc. 117, 4199 (1995)CrossRefGoogle Scholar
  53. 53.
    R. Hülnhagen, H. Baumgärtel, J. Electroanal. Chem. 98, 119 (1979)CrossRefGoogle Scholar
  54. 54.
    K. Pekmez, H. Özyöruk, A. Yildiz, Ber. Bunsenges. Phys. Chem. 96, 1805 (1992)CrossRefGoogle Scholar
  55. 55.
    T. Sakamoto, T. Nagano, Y. Kondo, H. Yamanaka, Synthesis 3, 215 (1990)CrossRefGoogle Scholar
  56. 56.
    Y. Iwanami, Bull. Chem. Soc. Jpn. 44, 1311 (1971)CrossRefGoogle Scholar
  57. 57.
    S.K. Khetan, J.G. Hiriyakkanavar, M.V. George, Tetrahedron 24, 1567 (1968)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2020

Authors and Affiliations

  • Ameneh Abolghassemi Fakhree
    • 1
  • Roghayeh Mohammadzadeh
    • 1
  • Esmaeel Alipour
    • 2
  • Zarrin Ghasemi
    • 1
    Email author
  1. 1.Department of Organic and Biochemistry, Faculty of ChemistryUniversity of TabrizTabrizIran
  2. 2.Department of Analytical Chemistry, Faculty of ChemistryUniversity of TabrizTabrizIran

Personalised recommendations