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Disazo dyes containing pyrazole and benzothiazole moieties: synthesis, characterization, absorption characteristics and tautomeric structures

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Abstract

Eight newly synthesized disazo disperse dyes containing benzothiazole and pyrazole moieties were prepared by diazotization of 2-aminobenzothiazole, coupling with 3-aminocrotononitrile as active methylene, cyclization reactions with hydrazine hydrate and phenyl hydrazine, diazotization again and finally coupling with dimedone, dioxane, 1-methyl imidazole and 2-methyl imidazole, respectively. Their structures were characterized with spectroscopic methods (FT-IR, 1H-NMR, 13C-NMR) and solvatochromic properties were studied with UV–Vis spectroscopy in different solvents. Tautomeric structures of synthesized dyes were also examined in detail.

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References

  1. H. Motiei, A. Jafari, R. Naderali, Opt. Laser Technol. 88, 68 (2017)

    Article  CAS  Google Scholar 

  2. A. Saylam, Z. Seferoğlu, N. Ertan, J. Mol. Liq. 195, 267 (2014)

    Article  CAS  Google Scholar 

  3. F. Yıldırım, A. Demirçalı, F. Karcı, A. Bayrakdar, P.T. Taşlı, H.H. Kart, J. Mol. Liq. 223, 557 (2016)

    Article  Google Scholar 

  4. Ç. Karabacak, T. Tilki, B. Özden Tuncer, M. Cengiz, Res. Chem. Intermed. 41(4), 1985 (2015)

    Article  CAS  Google Scholar 

  5. Ç. Karabacak Atay, M. Gökalp, B. Özden Tuncer, T. Tilki, J. Macromol. Sci. A 54(4), 236 (2017)

    Article  CAS  Google Scholar 

  6. F. Karcı, F. Karcı, Dyes Pigm. 76, 97 (2008)

    Article  Google Scholar 

  7. L. Chen, Y. Cui, G. Qian, M. Wang, Dyes Pigm. 73(3), 338 (2007)

    Article  CAS  Google Scholar 

  8. G. Pavlovic, L. Racane, H. Cicak, V. Tralic´-Kulenovic´, Dyes Pigm. 83, 354 (2009)

    Article  CAS  Google Scholar 

  9. S. Harisha, J. Keshavayya, B.E.K. Swamy, C.C. Viswanath, Dyes Pigm. 136, 742 (2017)

    Article  CAS  Google Scholar 

  10. K.M. Khan, M.A. Mesaik, O.M. Abdalla, F. Rahim, S. Soomro, S.A. Halim, G. Mustafa, N. Ambreen, A.S. Khalid, M. Taha, S. Perveen, M. Tanveer Alam, A. Hameed, Z. Ul-Haq, H. Ullah, Z.U. Rehman, R.A. Siddiqui, W. Voelter, Bioorg. Chem. 64, 21 (2016)

    Article  CAS  Google Scholar 

  11. M.T. Gabr, N.S. El-Gohary, E.R. El-Bendary, M.M. El-Kerdawy, N. Ni, M.I. Shaaban, Chin. Chem. Lett. 26, 1522 (2015)

    Article  CAS  Google Scholar 

  12. A.K. El-Damasy, J.H. Lee, S.H. Seo, N.C. Cho, A.N. Pae, G. Keum, Eur. J. Med. Chem. 115, 201 (2016)

    Article  CAS  Google Scholar 

  13. S. Ke, Y. Wei, Z. Yang, K. Wang, Y. Liang, L. Shi, Bioorgan. Med. Chem. Lett. 23, 5131 (2013)

    Article  CAS  Google Scholar 

  14. V.N. Telvekar, V.K. Bairwa, K. Satardekar, A. Bellubi, Bioorgan. Med. Chem. Lett. 22, 649 (2012)

    Article  CAS  Google Scholar 

  15. V.S. Patil, K.P. Nandre, S. Ghosh, V.J. Rao, B.A. Chopade, B. Sridhar, S.V. Bhosale, S.V. Bhosale, Eur. J. Med. Chem. 59, 304 (2013)

    Article  CAS  Google Scholar 

  16. J. Ma, G. Bao, L. Wang, W. Li, B. Xu, B. Du, J. Lv, X. Zhai, P. Gong, Eur. J. Med. Chem. 96, 173 (2015)

    Article  CAS  Google Scholar 

  17. I.V. Taydakov, A.A. Akkuzina, R.I. Avetisov, A.V. Khomyakov, R.R. Saifutyarov, I.C. Avetissov, J. Lumin. 177, 31 (2016)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science and Arts, Süleyman Demirel University, 32260, Isparta, Turkey

    Gülşah Ciçen & Tahir Tilki

  2. Basic Education Department, Education Faculty, Mehmet Akif Ersoy University, 15030, Burdur, Turkey

    Çiğdem Karabacak Atay

Authors
  1. Gülşah Ciçen
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  2. Çiğdem Karabacak Atay
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  3. Tahir Tilki
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Correspondence to Tahir Tilki.

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Ciçen, G., Karabacak Atay, Ç. & Tilki, T. Disazo dyes containing pyrazole and benzothiazole moieties: synthesis, characterization, absorption characteristics and tautomeric structures. Res Chem Intermed 43, 6803–6816 (2017). https://doi.org/10.1007/s11164-017-3021-5

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  • DOI: https://doi.org/10.1007/s11164-017-3021-5

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