SYNTHESIS AND CHARACTERIZATION OF DYES DERIVED FROM 1-AMINOANTHRAQUINONE
DOI:
https://doi.org/10.63996/njte.v25i1.72Keywords:
1-Aminoanthraquinone, Synthesis, Dyes, Characterization, ColourantsAbstract
This study investigated the synthesis and characterization of three anthraquinone-based dyes derived from 1-aminoanthraquinone through diazotization and coupling reactions using H-acid, J-acid, and γ-acid as coupling agents. Diazotization was carried out by reacting 1-aminoanthraquinone (0.89 g, 0.004 mol) with sodium nitrite (0.28 g, 0.004 mol) in hydrochloric acid at 0–5°C to form a diazonium salt, which was subsequently coupled with H-acid, J-acid, and γ-acid to produce Dye A, Dye B, and Dye C, respectively. The synthesized dyes were characterized using UV–Visible spectroscopy, Fourier Transform Infrared (FTIR) spectroscopy, melting point determination, and solubility tests. Dye A and Dye C exhibited orange coloration, while Dye B was maroon. Melting points ranged from 279.4°C to 321.2°C, indicating high thermal stability. Percentage yields were 99.98%, 87.02%, and 97.29% for Dyes A, B, and C, respectively. UV–Visible analysis revealed absorption maxima at 474, 477, and 466 nm for Dyes A, B, and C, respectively, corresponding to π→π* electronic transitions. The FTIR spectra confirmed the presence of O–H and N–H stretching vibrations in Dyes A and C, strong C=N and O–H (carboxylic) bands in Dye B and aromatic C=C and C=O stretches across all samples, verifying successful coupling and anthraquinone framework integrity. Solubility tests in methanol, distilled water, propanol and hydrochloric acid revealed high solubility in polar solvents and limited solubility in less polar or acidic media, consistent with the presence of hydroxyl and sulfonic groups. As such, these results demonstrate that 1-aminoanthraquinone is a suitable precursor for synthesizing thermally stable, vividly coloured, and thermally stable and vividly coloured dyes with potential applications in textile, polymer and optoelectronic industries.
References
Ajayi, O. A., & Olatunji, G. A. (2016). Synthesis, characterization and antibacterial activity of some anthraquinone dye derivatives. Journal of Baic and Applied Research International, 17, 280-289.
Celik, S., Vagifli, F., Akyuz, S., Ozkok, F., E. Ozel, A., Dosler, S., & Onul, N. (2022). Synthesis, vibrational spectroscopic investigation, molecular docking, antibacterial and antimicrobial studies of a new anthraquinone derivative compound. Spectroscopy Letters, 55(4), 259-277.
Choudhary, S., Gupta, V., Kaur, P., & Thind, T. S. (2025). Anthraquinones: Integrated Perspectives on Analytical Methodologies and Functional Applications. In Anthraquinones: Bioactive Multifaceted Therapeutic Agents (pp. 1-59). Bentham Science Publishers.
Gupta, P. O., & Sekar, N. (2024). NLOphoric anthraquinone dyes–a review. ChemistrySelect, 9(20), e202400736.
Li, Y., Tan, T., Wang, S., Xiao, Y., & Li, X. (2017). Highly solvatochromic fluorescence of anthraquinone dyes based on triphenylamines. Dyes and Pigments, 144, 262-270.
Liu, Y. Q., Maulidiany, N., Zeng, P., & Heo, S. (2021). Decolourization of azo, anthraquinone and triphenylmethane dyes using aerobic granules: Acclimatization and long-term stability. Chemosphere, 263, 128312.
Masilamani, G., Batchu, H., Amsallem, D., & Bedi, A. (2022). Novel series of diaminoanthraquinone-based π-extendable building blocks with tunable optoelectronic properties. ACS omega, 7(29), 25874-25880.
Myek, B., Sunday, N., & Agbamu, O. F. (2021). Synthesis and characterization of an azo dye and its iron complex. FUDMA journal of sciences, 5(4), 347-352.
Obi, J. C., Emmanuel, I. V., Okoro, L. N., Bolade, A. O., Onuh, E. F., & Ndulaka, J. C. (2022). Synthesis, spectroscopic studies and fastness properties of monoazo dyes derived from substituted arylamines. Science World Journal, 17(1), 143-147.
Penthala, R., Kumar, R. S., Heo, G., Kim, H., Lee, I. Y., Ko, E. H., & Son, Y. A. (2019). Synthesis and efficient dyeing of anthraquinone derivatives on polyester fabric with supercritical carbon dioxide. Dyes and Pigments, 166, 330-339.
Perkampus, H. H. (2013). UV-VIS Spectroscopy and its Applications. Springer Science & Business Media.
Pishgar, M., Gharanjig, K., Yazdanshenas, M. E., Farizadeh, K., & Rashidi, A. (2022). Synthesis and characterization of novel fluorescent reactive dyes for dyeing of cotton fabrics. The Journal of The Textile Institute, 113(4), 595-605.
Riaz, S., Jabbar, A., Khaskheli, S., Sagheer, S., & Choudhary, M. I. (2023). Anthraquinone based anti-UV acid-azo dyes; a study of their synthesis, fastness, and UV-protection properties. Journal of Molecular Structure, 1272, 134219.
Rotich, V., Wangila, P., & Cherutoi, J. (2022). FT‐IR Analysis of Beta vulgaris Peels and Pomace Dye Extracts and Surface Analysis of Optimally Dyed‐Mordanted Cellulosic Fabrics. Journal of Chemistry, 2022(1), 2233414.
Routoula, E., & Patwardhan, S. V. (2020). Degradation of anthraquinone dyes from effluents: a review focusing on enzymatic dye degradation with industrial potential. Environmental science & technology, 54(2), 647-664.
Shahab, S., Filippovich, L., Sheikhi, M., Yahyaei, H., Aharodnikova, M., Kumar, R., & Khaleghian, M. (2017). Spectroscopic (polarization, excitedstate, FT-IR, UV/Vis and 1H NMR) and thermophysical investigations of new synthesized azo dye and its application in polarizing film. Am. J. Mater. Synth. Process, 5, 17-23.
Takeda, T., Kasahara, Y., & Akutagawa, T. (2021). Color-tunable arylaminoanthraquinone dyes through hydrogen-bond-assisted charge transfer interaction. RSC advances, 11(39), 24217-24231.
Wang, Z., Li, C., Zhang, H., & Liu, Z. (2018). 1-Aminoanthraquinone diazonium salt on the coupling modification dyeing of silk fibroin with enhanced color fastness. Fibers and Polymers, 19(10), 2134-2138.
Zafar, S., Bukhari, D. A., & Rehman, A. (2022). Azo dyes degradation by microorganisms–An efficient and sustainable approach. Saudi Journal of Biological Sciences, 29(12), 103437.
Zhou, F., Cai, L., Ye, W., Zhu, K., Li, J., Li, Y., Xu, W., Wang, P. & Duanmu, C. (2023). Efficient and controllable synthesis of 1-aminoanthraquinone via high-temperature ammonolysis using continuous-flow method. Molecules, 28(11), 4314.
