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

Year 2026, Volume: 30 Issue: 1 , 184 - 190 , 24.04.2026

Nesrin Şener , Ali Basim Shihab Shihab , Merve Zurnacı , İzzet Şener

https://doi.org/10.19113/sdufenbed.1810211

https://izlik.org/JA88PT24FS

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.

Keywords

Pyrazole , thiadiazole , azo dyes , solvatochromic

Ethical Statement

In this study, we undertake that all the rules required to be followed within the scope of the "Higher Education Institutions Scientific Research and Publication Ethics Directive" are complied with, and that none of the actions stated under the heading "Actions Against Scientific Research and Publication Ethics" are not carried out.

Supporting Institution

Kastamonu University

Project Number

KÜ-BAP01/2021-37

Thanks

The authors are grateful to the Scientific Research Projects Council of Kastamonu University (KÜ-BAP01/2021-37).

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

https://izlik.org/JA88PT24FS

Abstract

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.

Keywords

Pirazol , tiyadiazol , azo boyarmadde , solvatokromik

Ethical Statement

Bu çalışmada, “Yükseköğretim Kurumları Bilimsel Araştırma ve Yayın Etiği Yönergesi” kapsamında uyulması gerekli tüm kurallara uyulduğunu, bahsi geçen yönergenin “Bilimsel Araştırma ve Yayın Etiğine Aykırı Eylemler” başlığı altında belirtilen eylemlerden hiçbirinin gerçekleştirilmediğini taahhüt ederiz.

Supporting Institution

Kastamonu Üniversitesi

Project Number

KÜ-BAP01/2021-37

Thanks

Yazarlar Kastamonu Üniversitesi Bilimsel Araştırma Projeleri Kuruluna (KÜ-BAP01/2021-37) teşekkürlerini sunarlar.

References

• [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.