Nove azo boje izvedene iz piridona: sinteza, strukturna karakterizacija i solvatohromna svojstva
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Jul 17, 2026
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Luka Matović
http://orcid.org/0000-0003-4945-7776
Vojkan Stamenković
Jelena Lađarević
http://orcid.org/0000-0002-5554-7295
Nemanja Trišović
http://orcid.org/0000-0002-9231-4810
Anita Lazić
http://orcid.org/0000-0003-4855-3782
Aleksandra Mašulović
http://orcid.org/0000-0002-5279-7694
Dušan Mijin
http://orcid.org/0000-0001-5691-2971
http://orcid.org/0000-0003-4945-7776
Vojkan Stamenković
Jelena Lađarević
http://orcid.org/0000-0002-5554-7295
Nemanja Trišović
http://orcid.org/0000-0002-9231-4810
Anita Lazić
http://orcid.org/0000-0003-4855-3782
Aleksandra Mašulović
http://orcid.org/0000-0002-5279-7694
Dušan Mijin
http://orcid.org/0000-0001-5691-2971
Apstrakt
Azo boje predstavljaju najznačajniju klasu organskih boja zahvaljujući svojoj strukturnoj raznovrsnosti, podesivim svojstavima i širokom spektru primena u različitim naučnim i industrijskim oblastima. Heterociklične azo boje predstavljaju značajnu potklasu ovih jedinjenja, pri čemu se posebno izdvajaju azo boje na bazi piridona zbog jednostavne sinteze, visoke funkcionalnosti i visokih vrednosti molarnog ekstinkcionog koeficijenta (ε). U ovom radu izvršena je sinteza i detaljna karakterizacija dva nova molekula azo boja izvedenih iz piridona. Boje su dobijene reakcijom diazotovanja anilina i 4-aminofenola, a zatim reakcijom diazo-kuplovanja sa novim 4-(piridin-3-il)-6-hidroksi-3-cijano-2-piridonom. Oba jedinjenja su okarakterisana temperaturom topljenja, ATR-FTIR i 1H NMR spektroskopijom. UV-Vis spektroskopija korišćena je za ispitivanje solvatohromnih i tautomernih svojstava ovih jedinjenja u setu rastvarača različite polarnosti. Pored toga, ispitivano je i dejstvo pH vrednosti rastvarača na tautomernu ravnotežu ovih jedinjenja (kiselo-bazna ravnoteža).
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Kako citirati
MATOVIĆ, Luka et al.
Nove azo boje izvedene iz piridona: sinteza, strukturna karakterizacija i solvatohromna svojstva.
Zbornik Međunarodnog kongresa o procesnoj industriji – Procesing, [S.l.], v. 39, n. 1, p. 99-110, july 2026.
Dostupno na: <http://izdanja.smeits.rs/index.php/ptk/article/view/8338>. Datum pristupa: 07 aug. 2026
doi: https://doi.org/10.24094/ptk.026.1.099.
Sekcija
Procesne tehnologije, operacije, aparati i mašine u procesnoj industriji
Reference
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[9] Mašulović, A., J. Lađarević, J. Lović, V. Vitnik, Ž. Vitnik, M. Avramov Ivić, D. Mijin, Comparative experimental and DFT study of the electrochemical oxidation of azo pyridone dyes, Journal of Electroanalytical Chemistry, 983 (2025), 119043.
[10] Sorokin, S. P., M Y. Ievlev, O V. Ershov, 2-Pyridone-based stilbazoles containing cyano and trifluoromethyl acceptors: Synthesis and fluorescence properties in solutions and in solid state, Dyes and Pigments, 219 (2023), 111581.
[11] Clarke, K., K. Rothwell, A Kinetic Study of the Effect of Substituents on the Rate of Formation of Alkylpyridinium Halides in Nitromethane Solution, Journal of the Chemical Society, 1960, pp. 1885–1895.
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[13] Hurtado-Rodríguez, D., A. Salinas-Torres, H. Rojas , D. Becerra, J.-C. Castillo, Bioactive 2-pyridone-containing heterocycle syntheses using multicomponent reactions, Royal Society of Chemistry Advances, 12 (2022), pp. 35158-35176
[14] Dračínsky, M., L. Čechova, P. Hodgkinson, Prochazkova, Z. Janeba, Resonance-assisted stabilisation of hydrogen bonds probed by NMR spectroscopy and path integral molecular dy-namics, Chemical Communications, 51 (2015), 13986.
[15] Yaman, M.,, E. Özsoy, M. Yahya, H. Tezcan, Spectroscopic determination of the acidity con-stants and the effects of pH, temperature and solvents on the tautomerism of 1-substituted phenyl-3,5-diphenylformazans, Chemical Physics, 573 (2023), 111979.
[16] Kaştaş G., Ç. A. Kaştaş, A. Tabak, Investigation of molecular structure and sol-vent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV–vis, NMR and DFT methods, Spectrochimica Acta Part A: Molecular and Biomolecular Spectros-copy, 222 (2019), 117198.
[17] Ghanadzadeh G. A., M. Moghadam, M.S. Zakerhamidi, E. Moradi, Solvatochromism, tau-tomerism and dichroism of some azoquinoline dyes in liquids and liquid crystals, Dyes and Pig-ments, 92 (2012), 3, pp. 1320-1330.
[18] Ozen, A. S., P. Doruker, V. Aviyente, Effect of cooperative hydrogen bonding in azo-hydrazone tautomerism of azo dyes, Journal of Physical Chemistry A, 111 (2007), 51, pp. 13506-14.
[19] De Melo, C. E. A., Celso R. N., Leandro G. N., Felipe S. S. S., Robson da S. O., Giovanni F. C., Vanderlei G. M., Solvatochromism of new substituted 4-[(E)-(4-nitrophenyl)diazenyl] phenolate dyes, Journal of Molecular Liquids, 301 (2020), 112330.
[20] Lađarević, J., Bojan B., Luka M., Biljana B. N., Dušan Mijin, Role of the bifurcated intra-molecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes, Dyes and Pigments, 162 (2019), pp. 562–572.
[2] Salaman, M., Abdul J., Salma F., Idrees B., Muhammad S. K. R., New heterocyclic azo-disperse dyes; their synthesis, characterization, application, photo physical properties and solva-tochromic studies, Journal of Molecular Structure, 1287 (2023), 135664.
[3] Alsantali, R. I., Q. A. Raja, A. Y.A. Alzahrani, A. Sadiq, N. Naeem, E. U. Mughal, M. M. Al-Rooqi, N. El Guesmi, Z. Moussa, S. A. Ahmed, Miscellaneous azo dyes: a comprehensive review on recent advancements in biological and industrial applications, Dyes and Pigments, 199 (2022), 110050.
[4] Maliyappa, M.R., J. Keshavayya, M.S. Sudhanva, I. Pushpavathi, V. Kumar, Heterocyclic azo dyes derived from 2-(6-chloro-1,3-benzothiazol-2-yl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one having benzothiazole skeleton: Synthesis, structural, computational and biological studies, Journal of Molecular Structure, 1247, (2022), 131321.
[5] Karci, F., F. Karci, A. Demirçali, M. Yamaç, Synthesis, solvatochromic properties and antimi-crobial activities of some novel pyridone-based disperse disazo dyes, Journal of Molecular Liq-uids, 187 (2013), pp. 302-308.
[6] Belowar, S., A. Jalil, Recent advancements in the chemistry of 1,3,4-Thiadiazole ring-containing azo dyes, Next Materials, 11 (2026), 101794.
[7] Tadić, J., J. Lađarević, Ž. Vitnik, V. Vitnik, T. Stanojković, I. Matić, D. Mijin, Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer ac-tivity, Dyes and Pigments, 187 (2021), 109123.
[8] Ghanavatkar, C. W., V. Mishra, N. Sekar, Benzothiazole-pyridone and benzothiazole-pyrazole clubbed emissive azo dyes and dyeing application on polyester fabric: UPF, biological, photophysical and fastness properties with correlative computational assessments, Spectro-chimica Acta Part A: Molecular and Biomolecular Spectroscopy, 230 (2020), 5, 118064.
[9] Mašulović, A., J. Lađarević, J. Lović, V. Vitnik, Ž. Vitnik, M. Avramov Ivić, D. Mijin, Comparative experimental and DFT study of the electrochemical oxidation of azo pyridone dyes, Journal of Electroanalytical Chemistry, 983 (2025), 119043.
[10] Sorokin, S. P., M Y. Ievlev, O V. Ershov, 2-Pyridone-based stilbazoles containing cyano and trifluoromethyl acceptors: Synthesis and fluorescence properties in solutions and in solid state, Dyes and Pigments, 219 (2023), 111581.
[11] Clarke, K., K. Rothwell, A Kinetic Study of the Effect of Substituents on the Rate of Formation of Alkylpyridinium Halides in Nitromethane Solution, Journal of the Chemical Society, 1960, pp. 1885–1895.
[12] Brown, B. B., K. S. Rehder, Prenylation Inhibitors and Methods of Their Synthesis and Use, WO 2004/016592, PCT/US2003/024985, 2003.
[13] Hurtado-Rodríguez, D., A. Salinas-Torres, H. Rojas , D. Becerra, J.-C. Castillo, Bioactive 2-pyridone-containing heterocycle syntheses using multicomponent reactions, Royal Society of Chemistry Advances, 12 (2022), pp. 35158-35176
[14] Dračínsky, M., L. Čechova, P. Hodgkinson, Prochazkova, Z. Janeba, Resonance-assisted stabilisation of hydrogen bonds probed by NMR spectroscopy and path integral molecular dy-namics, Chemical Communications, 51 (2015), 13986.
[15] Yaman, M.,, E. Özsoy, M. Yahya, H. Tezcan, Spectroscopic determination of the acidity con-stants and the effects of pH, temperature and solvents on the tautomerism of 1-substituted phenyl-3,5-diphenylformazans, Chemical Physics, 573 (2023), 111979.
[16] Kaştaş G., Ç. A. Kaştaş, A. Tabak, Investigation of molecular structure and sol-vent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV–vis, NMR and DFT methods, Spectrochimica Acta Part A: Molecular and Biomolecular Spectros-copy, 222 (2019), 117198.
[17] Ghanadzadeh G. A., M. Moghadam, M.S. Zakerhamidi, E. Moradi, Solvatochromism, tau-tomerism and dichroism of some azoquinoline dyes in liquids and liquid crystals, Dyes and Pig-ments, 92 (2012), 3, pp. 1320-1330.
[18] Ozen, A. S., P. Doruker, V. Aviyente, Effect of cooperative hydrogen bonding in azo-hydrazone tautomerism of azo dyes, Journal of Physical Chemistry A, 111 (2007), 51, pp. 13506-14.
[19] De Melo, C. E. A., Celso R. N., Leandro G. N., Felipe S. S. S., Robson da S. O., Giovanni F. C., Vanderlei G. M., Solvatochromism of new substituted 4-[(E)-(4-nitrophenyl)diazenyl] phenolate dyes, Journal of Molecular Liquids, 301 (2020), 112330.
[20] Lađarević, J., Bojan B., Luka M., Biljana B. N., Dušan Mijin, Role of the bifurcated intra-molecular hydrogen bond on the physicochemical profile of the novel azo pyridone dyes, Dyes and Pigments, 162 (2019), pp. 562–572.