Synthesis, Characterization and Investigation of Absorption Properties of Hydroxy Benzoic Acid Substituted Disazo Dyes

Abstract

In this study, new hydroxybenzoic acid substituted disazo dyes with heterocycle, which has become a remarkable research topic due to its versatile applications, were synthesized. In the first stage of the study, diazonium salts of some aromatic amine groups were obtained and azo coupling reaction was carried out with 3-aminocrotononitrile. As a result of the cyclization reaction of the obtained 1a-e compounds with hydrazinemonahydrate, 2a-e mono azo dyes were synthesized.In the second stage of the study, 2,4-dihydroxy benzoic acid and 3,5-dihydroxy benzoic acid compounds were used as coupling components and the structural properties of the new disazo dyes (3a-e, 4a-e) were characterized by spectroscopic analysis methods of FT-IR and 1H-NMR and melting points were determined. In order to investigate the solvent effect on the absorption spectra of the synthesized compounds, the absorption spectra on the visible region in acetic acid, dimethyl formamide, dimethyl sulfoxide, chloroform and methanol and the variation of the maximum absorption wavelengths in these solvents were investigated.

Keywords

• Disazo dye
• 3-aminocrotononitrile
• Azo-Coupling reaction
• Dihydroxybenzoic acid

Hidroksi Benzoik Asit Sübstitüeli Disazo Boyarmaddelerin Sentezi, Karakterizasyonu ve Absorpsiyon Özelliklerinin İncelenmesi

Abstract

Bu çalışmada, çok yönlü uygulamaları nedeniyle dikkat çeken bir araştırma konusu haline gelen heterohalkaya sahip yeni hidroksi benzoik asit sübstitüeli disazo boyarmaddeler sentezlenmiştir. Çalışmanın ilk aşamasında bazı aromatik amin gruplarının diazonyum tuzları elde edilmiş ve 3-aminokrotononitril ile azo kenetlenme reaksiyonu yapılmıştır. Elde edilen 1a-e bileşiklerinin hidrazinmonahidrat ile halkalaşma reaksiyonu sonucu 2a-e mono azo boyarmaddeler sentezlenmiştir. Çalışmanın ikinci aşamasında ise kenetleme bileşeni olarak 2,4-dihidroksi benzoik asit ve 3,5-dihidroksi benzoik asit bileşikleri kullanılmış olup, elde edilen yeni disazo boyarmaddelerin (3a-e, 4a-e) yapısal özellikleri FT-IR ve 1H-NMR spektroskopik analiz yöntemleri ile karakterize edilmiş ve erime noktaları belirlenmiştir. Sentezlenen bileşiklerin absorpsiyon spektrumları üzerindeki çözücü etkisini araştırmak için asetik asit, dimetil formamid, dimetil sülfoksit, kloroform ve metanolde görünür bölge üzerindeki absorpsiyon spektrumları ve bu çözücülerdeki maksimum absorpsiyon dalga boylarının değişimi araştırılmıştır.

Keywords

• Disazo boya
• 3-aminokrotononitril
• Azo-Kenetlenme reaksiyonu
• Dihidroksibenzoik asit

References

1. Gordon, P.F., Gregory, P. 1987. Azo dyes. In Organic chemistry in colour. Springer, Berlin, Heidelberg, 95-162s.
2. Başer, İ., İnanıcı Y. 1990. Boyarmadde Kimyası, Marmara Üniversitesi Teknik Eğitim Fakültesi, İstanbul, 482s.
3. Karcı, F., & Karcı, F. 2012. Synthesis and tautomeric structures of some novel thiophene-based bis-heterocyclic monoazo dyes. Journal of Molecular Structure, 1024, 117-122. DOI: 10.1016/j.molstruc.2012.05.021
4. Hunger, K. 2003. Industrial dyes: chemistry, properties, applications. Wiley-VCH Weinheim, 653s.
5. Youssef, Y. A., Kamel, M. M., Taher, M. S., Ali, N. F., & Abd El Megiede, S. A. 2014. Synthesis and application of disazo reactive dyes derived from sulfatoethylsulfone pyrazolo [1, 5-a] pyrimidine derivatives. Journal of Saudi Chemical Society, 18(3), 220-226. DOI: 10.1016/j.jscs.2011.06.015
6. Yazdanbakhsh, M. R., Ghanadzadeh, A., & Moradi, E. 2007. Synthesis of some new azo dyes derived from 4-hydroxy coumarin and spectrometric determination of their acidic dissociation constants. Journal of Molecular Liquids, 136(1-2), 165-168. DOI: 10.1016/j.molliq.2007.03.005
7. Ramugade, S. H., Warde, U. S., & Sekar, N. 2019. Azo dyes with ESIPT core for textile applications and DFT study. Dyes and Pigments, 170, 107626. DOI: 10.1016/j.dyepig.2019.107626
8. Demirçalı, A., Karcı, F., Avinc, O., Kahrıman, A. U., Gedik, G., & Bakan, E. 2019. The synthesis, characterization and investigation of absorption properties of disperse disazo dyes containing pyrazole and isoxazole. Journal of Molecular Structure, 1181, 8-13. DOI: 10.1016/j.molstruc.2018.12.033

9. Yıldırım, F., Demirçalı, A., Taşlı, P. T., & Karcı, F. 2021. New disazo dyes derived from aminopyrazoles: synthesis, spectroscopic properties, computational study and structural properties. Coloration Technology. DOI: 10.1111/cote.12524
10. Maliyappa, M. R., Keshavayya, J., Mahanthappa, M., Shivaraj, Y., & Basavarajappa, K. V. 2020. 6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: synthesis, characterization, electrochemical and DFT studies. Journal of Molecular Structure, 1199, 126959. DOI: 10.1016/j.molstruc.2019.126959
11. Gökalp, M., Dede, B., Tilki, T., & Atay, Ç. K. 2020. Triazole based azo molecules as potential antibacterial agents: Synthesis, characterization, DFT, ADME and molecular docking studies. Journal of Molecular Structure, 1212, 128140. DOI: 10.1016/j.molstruc.2020.128140
12. Atay, Ç. K., Tilki, T., & Dede, B. 2018. Design and synthesis of novel ribofuranose nucleoside analogues as antiproliferative agents: a molecular docking and DFT study. Journal of Molecular Liquids, 269, 315-326. DOI: 10.1016/j.molliq.2018.08.009.
13. Yıldırım, F., Demirçalı, A., Kiraz, A. Ö., & Karcı, F. 2020. Synthesis of some new pyrazolo [5, 1-c][1, 2, 4] triazine derivatives and computational study. Journal of Molecular Structure, 1222, 128850. DOI: 10.1016/j.molstruc.2020.128850
14. Sezgin, B., Tilki, T., Karabacak Atay, Ç., & Dede, B. 2020. Comparative in vitro and DFT antioxidant studies of phenolic group substituted pyridine-based azo derivatives. Journal of Biomolecular Structure and Dynamics, 1-12. DOI: 10.1080/07391102.2020.1863264.
15. Jarad, A. J., Majeed, I. Y., & Hussein, A. O. 2018. Synthesis and spectral studies of heterocyclic azo dye complexes with some transition metals. In Journal of Physics: Conference Series (Vol. 1003, No. 1, p. 012021). IOP Publishing. DOI: 10.1088/1742-6596/1003/1/012021.
16. Keshavayya, J., Pushpavathi, I., Keerthikumar, C. T., Maliyappa, M. R., & Ravi, B. N. 2020. Synthesis, characterization, computational and biological studies of nitrothiazole incorporated heterocyclic azo dyes. Structural Chemistry, 31(4), 1317-1329. DOI: 10.1007/s11224-020-01493-0.
17. Qiu, J., Xiao, J., Tang, B., Ju, B., & Zhang, S. 2019. Facile synthesis of novel disperse azo dyes with aromatic hydroxyl group. Dyes and Pigments, 160, 524-529. DOI: 10.1016/j.dyepig.2018.08.052.
18. Darabut, A. M., Purikova, O. H., & Lobko, Y. V. 2020. Synthesis of bis-azobenzene derivatives with reactive bromohexyl unit and carboxylic acid group based on Disperse Yellow 7. European Journal of Chemistry, 11(4), 298-303. DOI: 10.5155/eurjchem.11.4.298-303.2032.
19. Eyduran, F., & Yüzükırmızı, F. 2021. Synthesis and spectroscopic investigation of azo derivatives of 4, 6-dihydroxy-2-methylpyrimidine. Monatshefte für Chemie-Chemical Monthly, 1-7. DOI: 10.1007/s00706-021-02857-w
20. Otutu, J. O., & Osabohien, E. 2013. Synthesis and absorption spectra of monoazo dyes derived from 2-methoxy-5-nitroaniline. Asian J. Mater. Sci, 5, 1-8. DOI: 10.3923/ajmskr.2013.1.8.
21. Demirçalı, A., Karcı, F., & Sari, F. 2021. Synthesis and absorption properties of five new heterocyclic disazo dyes containing pyrazole and pyrazolone and their acute toxicities on the freshwater amphipod Gammarus roeseli. Coloration Technology, 137(3), 280-291. DOI: 10.1111/cote.12530.