Journals / Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi / 2026 / Cilt: 30 Sayı: 1

Synthesis of New Azo Dyes Containing Pyrazole and 1,3,4-Thiadiazole Derivatives and Investigation of Their Solvatochromic Properties

Pirazol ve 1,3,4-Tiyadiazol Türevlerini İçeren Yeni Azo Boyalarının Sentezi ve Solvatokromik Özelliklerinin İncelenmesi

Nesrin Şener(KASTAMONU ÜNİVERSİTESİ)0000-0001-5370-6048
Merve Zurnacı(KASTAMONU UNIVERSITY)0000-0002-2928-3492
İzzet Şener(KASTAMONU UNIVERSITY)0000-0003-0540-7523
Pages
184–190
Publication Date
2026-04-24
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

As a result of absorption studies, positive solvatochromism was observed in the synthesis compounds.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In this study, where 2-amino-1,3,4-thiadiazole and 5-mercapto-2-amino-1,3,4-thiadiazole compounds were used as starting materials, five new azo dyes were synthesized using 3-amino-5-methyl pyrazolone, 3-amino-1-phenyl-5-methyl pyrazolone, and barbutyric acid as coupling components. 1H-NMR and FT-IR spectroscopic methods determined the molecular structures of the synthesized compounds.
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Key Findings & Data:In addition, UV-Vis and absorption spectra of the synthesized compounds were taken, and their solvatochromic properties were investigated.
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Conclusion & Impact:As a result of absorption studies, positive solvatochromism was observed in the synthesis compounds.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Pirazol · tiyadiazol · azo boyarmadde

Abstract

In this study, where 2-amino-1,3,4-thiadiazole and 5-mercapto-2-amino-1,3,4-thiadiazole compounds were used as starting materials, five new azo dyes were synthesized using 3-amino-5-methyl pyrazolone, 3-amino-1-phenyl-5-methyl pyrazolone, and barbutyric acid as coupling components. 1H-NMR and FT-IR spectroscopic methods determined the molecular structures of the synthesized compounds. In addition, UV-Vis and absorption spectra of the synthesized compounds were taken, and their solvatochromic properties were investigated. As a result of absorption studies, positive solvatochromism was observed in the synthesis compounds.

Özet

2-amino-1,3,4-tiyadiazol ve 5-merkapto-2-amino-1,3,4-tiyadiazol bileşiklerinin başlangıç maddesi olarak kullanıldığı bu çalışmada; 3-amino-5-metil pirazolon, 3-amino-1-fenil-5-metil pirazolon ve barbütirik asitin kenetleme bileşenleri olarak kullanıldığı beş yeni azo boyarmadde sentezlenmiştir. Sentezlenen bileşiklerin moleküler yapıları 1H-NMR, FT-IR spektroskopik yöntemleri ile belirlenmiştir. Ayrıca, sentezlenen bileşiklerin UV-Vis. absorpsiyon spektrumları alınmış ve solvatokromik özellikleri incelenmiştir. Absorpsiyon çalışmaları sonucunda, sentezlenen bileşiklerde pozitif solvatokromizm gözlenmiştir.

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Cite This Article

Şener, N., Shihab, A. B. S., Zurnacı, M., Şener, İ. (2026). Synthesis of New Azo Dyes Containing Pyrazole and 1,3,4-Thiadiazole Derivatives and Investigation of Their Solvatochromic Properties. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, Cilt: 30 Sayı: 1, 184–190. https://doi.org/10.19113/sdufenbed.1810211

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References (33)

  1. Steenkamp, L., & Brady, D. (2003). Screening of commercial enzymes for the enantioselective hydrolysis of R, S-naproxen ester. Enzyme and microbial technology, 32(3-4), 472-477.
  2. Shinde, S. D., & Yadav, G. D. (2015). Insight into microwave assisted immobilized Candida antarctica lipase B catalyzed kinetic resolution of RS-(±)-ketorolac. Process Biochemistry, 50(2), 230-236.
  3. French, L. (2005). Dysmenorrhea. American family physician, 71(2), 285-291.
  4. Harrington, P. J., & Lodewijk, E. (1997). Twenty years of naproxen technology. Organic Process Research & Development, 1(1), 72-76.
  5. Rossi, S. (2006). Australian medicines handbook (pp. 143-145).
  6. Gür, M., Yerlikaya, S., Şener, N., Özkınalı, S., Baloglu, M. C., Gökçe, H.,. & Şener, İ. (2020). Antiproliferative-antimicrobial properties and structural analysis of newly synthesized Schiff bases derived from some 1, 3, 4-thiadiazole compounds. Journal of Molecular Structure, 1219, 128570.
  7. Hagar, M., Ahmed, H. A., Aljohani, G., & Alhaddad, O. A. (2020). Investigation of some antiviral N-heterocycles as COVID 19 drug: molecular docking and DFT calculations. International Journal of Molecular Sciences, 21(11), 3922.
  8. Cordell, G. A. (2008). The alkaloids: chemistry and biology (Vol. 65). Academic Press.
  9. Karthikeyan, S., Grishina, M., Kandasamy, S., Mangaiyarkarasi, R., Ramamoorthi, A., Chinnathambi, S.,. & John Kennedy, L. (2023). A review on medicinally important heterocyclic compounds and importance of biophysical approach of underlying the insight mechanism in biological environment. Journal of Biomolecular Structure and Dynamics, 41(23), 14599-14619.
  10. Şener, İ., Şahin, Ç., Demir, S., Şener, N., & Gür, M. (2020). A combined experimental and computational study of electrochemical and photophysical properties of new benzophenone derivatives functionalized with N-substituted-phenyl-1, 3, 4-thiadiazole-2-amine. Journal of Molecular Structure, 1203, 127475.
  11. Mohite, P., Bhoge, N., Dengale, S. G., & Darekar, N. R. (2024). Synthesis, Properties, and Biological Applications of 1, 2, 4-Thiadiazoles.
  12. Mittal, R. K., Mishra, R., Sharma, V., & Mishra, I. (2024). 1, 3, 4-thiadiazole: A versatile scaffold for drug discovery. Letters in Organic Chemistry, 21(5), 400-413.
  13. Özkınalı, S., Gür, M., Şener, N., Alkın, S., & Çavuş, M. S. (2018). Synthesis of new azo schiff bases of pyrazole derivatives and their spectroscopic and theoretical investigations. Journal of Molecular Structure, 1174, 74-83.
  14. Şener, N., Bayrakdar, A., Kart, H. H., & Şener, İ. (2017). A combined experimental and DFT investigation of disazo dye having pyrazole skeleton. Journal of Molecular Structure, 1129, 222-230.
  15. Dawood, K. M., Eldebss, T. M., El-Zahabi, H. S., Yousef, M. H., & Metz, P. (2013). Synthesis of some new pyrazole-based 1, 3-thiazoles and 1, 3, 4-thiadiazoles as anticancer agents. European journal of medicinal chemistry, 70, 740-749.
  16. Abdelhamid, A. O., Shawali, A. S., Gomha, S. M., & El-Enany, W. A. M. A. (2015). Synthesis and antimicrobial evaluation of some novel thiazole, 1, 3, 4-thiadiazole and pyrido [2, 3-d][1, 2, 4]-triazolo [4, 3-a] pyrimidine derivatives incorporating pyrazole moiety. Heterocycles, 91(11), 2126-2142.
  17. Rauf, M. A., & Hisaindee, S. (2013). Studies on solvatochromic behavior of dyes using spectral techniques. Journal of Molecular Structure, 1042, 45-56.
  18. Şener, İ., Karcı, F., Ertan, N., & Kılıç, E. (2006). Synthesis and investigations of the absorption spectra of hetarylazo disperse dyes derived from 2, 4-quinolinediol. Dyes and pigments, 70(2), 143-148.
  19. Geng, J., Dai, Y., Qian, H. F., Wang, N., & Huang, W. (2015). 2-Amino-4-chloro-5-formylthiophene-3-carbonitrile derived azo dyes. Dyes and Pigments, 117, 133-140.
  20. Warde, U., & Sekar, N. (2017). NLOphoric mono-azo dyes with negative solvatochromism and in-built ESIPT unit from ethyl 1, 3-dihydroxy-2-naphthoate: Estimation of excited state dipole moment and pH study. Dyes and Pigments, 137, 384-394.
  21. Seferoğlu, Z., Ertan, N., Hökelek, T., & Şahin, E. (2008). The synthesis, spectroscopic properties and crystal structure of novel, bis-hetarylazo disperse dyes. Dyes and Pigments, 77(3), 614-625.
  22. Özdemir, Ü. Ö., Aktan, E., Ilbiz, F., Gündüzalp, A. B., Özbek, N., Sarı, M.,. & Saydam, S. (2014). Characterization, antibacterial, anticarbonic anhydrase II isoenzyme, anticancer, electrochemical and computational studies of sulfonic acid hydrazide derivative and its Cu (II) complex. Inorganica Chimica Acta, 423, 194-203.
  23. Marini, A., Muñoz-Losa, A., Biancardi, A., & Mennucci, B. (2010). What is solvatochromism?. The Journal of Physical Chemistry B, 114(51), 17128-17135.
  24. Błasiak, B., Londergan, C. H., Webb, L. J., & Cho, M. (2017). Vibrational probes: From small molecule solvatochromism theory and experiments to applications in complex systems. Accounts of chemical research, 50(4), 968-976.
  25. Hemalatha, K., Madhumitha, G., Vasavi, C. S., & Munusami, P. (2015). 2, 3-Dihydroquinazolin-4 (1H)-ones: Visible light mediated synthesis, solvatochromism and biological activity. Journal of Photochemistry and Photobiology B: Biology, 143, 139-147.
  26. Kakanejadifard, A., Azarbani, F., Saki, Z., Kakanejadifard, S., & Zabardasti, A. (2014). Synthesis, characterization, solvatochromism and biological properties of 2, 2′-((1E, 1′ E)-((1, 2, 5-oxadiazole-3, 4-diyl) bis (azanylylidene)) bis (methan-ylylidene)) bis (4-(phenyldiazenyl) phenol). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 132, 700-705.
  27. Şener, N., & Aldwib, A. E. O. (2024). New Antibacterial 1, 3, 4‐Thiadiazole Derivatives With Pyridine Moiety. Chemistry & Biodiversity, 21(6), e202400522.
  28. Sharma, M., Sandhu, N., & Saraswat, V. (2024). Microwave assisted facile one pot synthesis of novel pyrazole derivative for multi-analyte detection (Fe3+ and Zn2+) and its solvatochromic studies. Journal of Molecular Structure, 1318, 139183.
  29. Zhu, H., Zhang, J., Zhang, H., Bai, J., Peng, J., & Jia, J. (2024). Triphenylamine-based 1, 3, 4-thiadiazole derivative: solvatochromism, aggregation-induced emission and reversible turn-on mechanofluorochromism. Journal of Luminescence, 267, 120390.
  30. Rezende, M. C., Dominguez, M., Aracena, A., & Millán, D. (2011). Solvatochromism and electrophilicity. Chemical Physics Letters, 514(4-6), 267-273.
  31. Gür, M., Yerlikaya, S., Şener, N., Özkınalı, S., Baloglu, M. C., Gökçe, H.,. & Şener, İ. (2020). Antiproliferative-antimicrobial properties and structural analysis of newly synthesized Schiff bases derived from some 1, 3, 4-thiadiazole compounds. Journal of Molecular Structure, 1219, 128570.
  32. Karthikeyan, S., Grishina, M., Kandasamy, S., Mangaiyarkarasi, R., Ramamoorthi, A., Chinnathambi, S.,. & John Kennedy, L. (2023). A review on medicinally important heterocyclic compounds and importance of biophysical approach of underlying the insight mechanism in biological environment. Journal of Biomolecular Structure and Dynamics, 41(23), 14599-14619.
  33. Özdemir, Ü. Ö., Aktan, E., Ilbiz, F., Gündüzalp, A. B., Özbek, N., Sarı, M.,. & Saydam, S. (2014). Characterization, antibacterial, anticarbonic anhydrase II isoenzyme, anticancer, electrochemical and computational studies of sulfonic acid hydrazide derivative and its Cu (II) complex. Inorganica Chimica Acta, 423, 194-203.