Synthesis of Some Azo Dyes Based on 2,3,3-Trimethyl-3H-indolenine

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dc.citation.epage556
dc.citation.issue3
dc.citation.spage549
dc.contributor.affiliationGeorgian Technical University
dc.contributor.affiliationSan Diego State University
dc.contributor.affiliationIvane Javakhishvili Tbilisi State University
dc.contributor.authorBukia, Tinatin
dc.contributor.authorUtiashvili, Mariam
dc.contributor.authorTsiskarishvili, Manana
dc.contributor.authorJalalishvili, Sopo
dc.contributor.authorGogolashvili, Ana
dc.contributor.authorTatrishvili, Tamara
dc.contributor.authorPetriashvili, Gia
dc.coverage.placenameЛьвів
dc.coverage.placenameLviv
dc.date.accessioned2024-02-12T08:52:10Z
dc.date.available2024-02-12T08:52:10Z
dc.date.created2023-02-28
dc.date.issued2023-02-28
dc.description.abstractНові азосполуки на основі 2,3,3-триметил-3Н-індоленіну синтезовано й охарактеризовано за допомогою ІЧ-, ЯМР- і мас-спектрального аналізу. Синтез проводили трьома різними маршрутами: 1) відновленням нітросполуки за допомогою Zn/NaOH у спирті; 2) нагріванням 2,3,3-триметил-3Н-індоленін-5-аміну в присутності MnO2 в толуолі; 3) діазотуванням 2,3,3-триметил-3Н-індоленін-5-аміну й обробкою отриманої солі діазонію відповідною азоскладовою.
dc.description.abstractNew azo compounds on the base of 2,3,3-trimethyl-3H-indolenine were synthesized and characterized by FT-IR, NMR, and Mas-spectral analysis. The synthesis was conducted in three different pathways: 1) by reducing the nitro compound with Zn/NaOH in alcohol; 2) by heating of 2,3,3-trimethyl-3H-indolenine-5-amine in the presence of MnO2 in toluene, and 3) by diazotization of 2,3,3-trimethyl-3H-indolenine-5-amine and treating the resulting diazonium salt with the appropriate coupler.
dc.format.extent549-556
dc.format.pages8
dc.identifier.citationSynthesis of Some Azo Dyes Based on 2,3,3-Trimethyl-3H-indolenine / Tinatin Bukia, Mariam Utiashvili, Manana Tsiskarishvili, Sopo Jalalishvili, Ana Gogolashvili, Tamara Tatrishvili, Gia Petriashvili // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2023. — Vol 17. — No 3. — P. 549–556.
dc.identifier.citationenSynthesis of Some Azo Dyes Based on 2,3,3-Trimethyl-3H-indolenine / Tinatin Bukia, Mariam Utiashvili, Manana Tsiskarishvili, Sopo Jalalishvili, Ana Gogolashvili, Tamara Tatrishvili, Gia Petriashvili // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2023. — Vol 17. — No 3. — P. 549–556.
dc.identifier.doidoi.org/10.23939/chcht17.03.549
dc.identifier.issn1196-4196
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/61286
dc.language.isoen
dc.publisherВидавництво Львівської політехніки
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofChemistry & Chemical Technology, 3 (17), 2023
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dc.relation.references[19] Karci, F.; Şener, N.; Yamaç, M.; Şener, İ.; Demirçali, A.A. The Synthesis, Antimicrobial Activity and Absorption Characteristics of Some Novel Heterocyclic Disazo Dyes. Dyes Pigm. 2009, 80, 47-52. https://doi.org/10.1016/j.dyepig.2008.05.001
dc.relation.references[20] Xu, H.; Zeng, X. Synthesis of Diaryl-Azo Derivatives as Potential Antifungal Agents. Bioorgan. Med. Chem. Lett. 2010, 20, 4193-4195. https://doi.org/10.1016/j.bmcl.2010.05.048
dc.relation.references[21] Liu, G.; Wang, X.; Hu, J.; Zhang, G.; Liu, S. Self-Immolative Polymersomes for High-Efficiency Triggered Release and Pro-grammed Enzymatic Reactions. J. Am. Chem. Soc. 2014, 136, 7492-7497. https://doi.org/10.1021/ja5030832
dc.relation.references[22] Mohamed-Smati, S.B.; Faraj, F.L.; Becheker, I.; Berredjem, H.; Bideau, F.L.; Hamdi, M.; Dumas, F.; Rachedi, Y. Synthesis, Characterization and Antimicrobial Activity of Some New Azo Dyes Derived from 4-Hydroxy-6-methyl-2H-pyran-2-one and its Dihydro Derivative. Dyes Pigm. 2021, 188, 109073. https://doi.org/10.1016/j.dyepig.2020.109073
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dc.relation.references[28] Naji, A.M.; Abdula, A.M.; Nief O.A.; Abdullah, E.K. Synthe-sis, Characterization, Antimicrobial and Molecular Docking Study of Benzooxadiazole Derivatives. Chem. Chem. Technol. 2022, 16, 25-33. https://doi.org/10.23939/chcht16.01.025
dc.relation.references[29] Kulkarni, M.; Thakur, P. The Effect of UV/TiO2/H2O2 Process and Influence of Operational Parameters on Photocatalytic Degrada-tion of Azo Dye in Aqueous TiO2 Suspension. Chem. Chem. Tech-nol. 2010, 4, 265-270. https://doi.org/10.23939/chcht04.04.265
dc.relation.references[30] Gilbert, A.M.; Failli, A.; Shumsky, J.; Yang, Y.; Severin, A.; Singh, G.; Hu, W.; Keeney, D.; Petersen, P.J.; Katz, A.H. Pyrazoli-dine-3,5-diones and 5-Hydroxy-1H-pyrazol-3(2H)-ones, Inhibitors of UDP-N-acetylenolpyruvyl Glucosamine Reductase. J. Med. Chem. 2006, 49, 6027-6036. https://doi.org/10.1021/jm060499t
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dc.relation.references[32] Piggott, H.A.; Hulme, Ch. Heterocyclic Nitrogen Compounds. US2016836, October 8, 1935.
dc.relation.references[33] Lyubich, M.S.; Isaev, S.G.; Al'perovich, M.A.; Shpileva, I.S.; Arshava, B.M. Interaction of 5-Amino-2,3-trimethyl-3H-indole with p-Nitrobenzaldehyde. Chem. Heterocycl. Compd. 1984, 20, 976-977. https://doi.org/10.1007/BF00506391
dc.relation.references[34] Bigelow, H.E.; Robinson, D.B. Azobenzene. Org. Synth. 1942, 22, 103. https://doi.org/10.15227/orgsyn.022.0028
dc.relation.references[35] Bhatnagar, I; George M.V. Oxidation of Phenylhydrazones with Manganese Dioxide. J. Org. Chem. 1967, 32, 2252-2256. https://doi.org/10.1021/jo01282a036
dc.relation.referencesen[1] Benkhaya, S.; Harfi, A. E.; El Harfi, A. Classifications, Proper-ties and Applications of Textile Dyes: A Review. Appl. J. Envir. Eng. Sci. 2017, 3, 311-320. https://doi.org/10.48422/IMIST.PRSM/ajees-v3i3.9681
dc.relation.referencesen[2] Mikroyannidis, J.A.; Tsagkournos, D.V.; Balraju, P.; Sharma G.D. Low Band Gap Dyes Based 3 on 2-Styryl-5-phenylazo-pyrrole: Synthesis and Application for Efficient Dye-Sensitized Solar Cells. J. Power Sources 2011, 196, 4152-4161. https://doi.org/10.1016/j.jpowsour.2010.12.038
dc.relation.referencesen[3] Al-Ahmad, A.Y.; Hassan, Q.M.A.; Badran, H.A.; Hussain, K.A. Investigating Some Linear and Nonlinear Optical Properties of the Azo Dye (1-Amino-2-hydroxy naphthalin sulfonic acid-[3-7(4-azo)]-4-amino diphenyl sulfone). Opt. Laser Technol. 2012, 44, 1450-1455. https://doi.org/10.1016/j.optlastec.2011.12.019
dc.relation.referencesen[4] Pevzner, E.; Ehrenberg, B. Principal Component Analysis of the Absorption and Resonance Raman Spectra of the Metallochromic Indicator Antipyrylazo III. Spectrochim. Acta A Mol. Biomol. Spec-trosc. 2000, 56, 637-651. https://doi.org/10.1016/S1386-1425(99)00164-X
dc.relation.referencesen[5] Feng, Y.; Liu, H.; Luo, W.; Liu, E.; Zhao, N.; Yoshino, K.; Feng, W. Covalent Functionalization of Graphene by Azobenzene with Molecular Hydrogen Bonds for Long-Term Solar Thermal Storage. Sci. Rep. 2013, 3, 3260. https://doi.org/10.1038/srep03260
dc.relation.referencesen[6] Adegoke, O.A.; Adesuji, T.E.; Thomas, O.E. Novel Colorimetric Sensors for Cyanide Based on Azo-Hydrazone Tautomeric Skeletons. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 128, 147-152. https://doi.org/10.1016/j.saa.2014.02.118
dc.relation.referencesen[7] Coelho, P.J.; Carvalho, L.M.; Fonseca, A.M.C.; Raposo, M.M.M. Photochromic Properties of Thienylpyrrole Azo in Solu-tion. Tetrahedron Lett. 2006, 47, 3711-3714. https://doi.org/10.1016/j.tetlet.2006.03.125
dc.relation.referencesen[8] Ruyffelaere, F.; Nardello, V.; Schmidt, R.; Aubry, J.M. Photo-sensitizing Properties and Reactivity of Aryl Azo Naphthol Dyes Towards Singlet Oxygen. J. Photochem. Photobiol. 2006, 183, 98-105. https://doi.org/10.1016/j.jphotochem.2006.02.029
dc.relation.referencesen[9] Erfantalab, M.; Khanmohammadi, H. New 1.2.4-Triazole-Based Azo–Azomethine Dye. Part III: Synthesis, Characterization, Ther-mal Property, Spectrophotometric and Computational Studies. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 125, 345-352. https://doi.org/10.1016/j.saa.2014.01.113
dc.relation.referencesen[10] Sabet, R.A.; Khoshsima, H. Real-Time Holographic Investiga-tion of Azo Dye Diffusion in a Nematic Liquid Crystal Host. Dyes Pigm. 2010, 87, 95-99. https://doi.org/10.1016/j.dyepig.2010.02.009
dc.relation.referencesen[11] Kim, Y.D.; Cho, J.H.; Park, C.R.; Choi, J.H.; Yoon, C.; Kim, J.P. Synthesis, Application and Investigation of Structure–Thermal Stability Relationships of Thermally Stable Water-Soluble azo Naphthalene Dyes for LCD Red Color Filters. Dyes Pigm. 2011, 89, 1-8. https://doi.org/10.1016/j.dyepig.2010.07.008
dc.relation.referencesen[12] Avella-Oliver, M.; Morais, S.; Puchades, R.; Maquieira, Á. Towards Photochromic and Thermochromic Biosensing. Trends Analyt. Chem. 2016, 79, 37-45 https://doi.org/10.1016/j.trac.2015.11.021
dc.relation.referencesen[13] Zhang, X.; Hou, L.; Samorı, P. Coupling Carbon Nanomateri-als with photochromic Molecules for the Generation of Optically Responsive Materials. Nat. Commun. 2016, 7, 11118. https://doi.org/10.1038/ncomms11118
dc.relation.referencesen[14] Benkhaya, S.; M'rabet, S.; El Harfi, A. Classifications, Proper-ties, Recent Synthesis and Applications of Azo Dyes. Heliyon 2020, 6, 03271. https://doi.org/10.1016/j.heliyon.2020.e03271
dc.relation.referencesen[15] Esser-Kahn, A.P.; Odom, S.A.; Sottos, N.R.; White, S.R.; Moore, J.S. Triggered Release from Polymer Capsules. Macromolecules 2011, 44, 5539-5553. https://doi.org/10.1021/ma201014n
dc.relation.referencesen[16] Yousefi, H.; Yahyazadeh, A.; Moradi Rufchahi, E.O.; Rassa, M. Synthesis, Spectral Properties, Biological Activity and Applica-tion of new 4-(Benzyloxy)phenol Derived Azo Dyes for Polyester Fiber Dyeing. J. Mol. Liq. 2013, 180, 51-58. https://doi.org/10.1016/j.molliq.2012.12.030
dc.relation.referencesen[17] Mallikarjuna, N.M.; Keshavayya, J. Synthesis, Spectroscopic Characterization and Pharmacological Studies on Novel Sulfamethaxazole Based Azo Dyes. J. King Saud Univ. Sci. 2020, 32, 251-259. https://doi.org/10.1016/j.jksus.2018.04.033
dc.relation.referencesen[18] Yazdanbakhsh, M.R.; Yousefi, H.; Mamaghani, M.; Moradi, E.O.; Rassa, M.; Pouramir, H.; Bagheri, M. Synthesis, Spectral Characterization and Antimicrobial Activity of Some New Azo 3 Dyes Derived from 4.6 Dihydroxypyrimidine, J. Mol. Liq. 2012, 169, 21-26. https://doi.org/10.1016/j.molliq.2012.03.003
dc.relation.referencesen[19] Karci, F.; Şener, N.; Yamaç, M.; Şener, İ.; Demirçali, A.A. The Synthesis, Antimicrobial Activity and Absorption Characteristics of Some Novel Heterocyclic Disazo Dyes. Dyes Pigm. 2009, 80, 47-52. https://doi.org/10.1016/j.dyepig.2008.05.001
dc.relation.referencesen[20] Xu, H.; Zeng, X. Synthesis of Diaryl-Azo Derivatives as Potential Antifungal Agents. Bioorgan. Med. Chem. Lett. 2010, 20, 4193-4195. https://doi.org/10.1016/j.bmcl.2010.05.048
dc.relation.referencesen[21] Liu, G.; Wang, X.; Hu, J.; Zhang, G.; Liu, S. Self-Immolative Polymersomes for High-Efficiency Triggered Release and Pro-grammed Enzymatic Reactions. J. Am. Chem. Soc. 2014, 136, 7492-7497. https://doi.org/10.1021/ja5030832
dc.relation.referencesen[22] Mohamed-Smati, S.B.; Faraj, F.L.; Becheker, I.; Berredjem, H.; Bideau, F.L.; Hamdi, M.; Dumas, F.; Rachedi, Y. Synthesis, Characterization and Antimicrobial Activity of Some New Azo Dyes Derived from 4-Hydroxy-6-methyl-2H-pyran-2-one and its Dihydro Derivative. Dyes Pigm. 2021, 188, 109073. https://doi.org/10.1016/j.dyepig.2020.109073
dc.relation.referencesen[23] Hunger, K.; Mischke, P. Azo Dyes, 1. Ullmann's encycl. ind. chem. 2011, 4, 523-541. https://doi.org/10.1002/14356007.a03_245.pub2
dc.relation.referencesen[24] Hunger, K.; Mischke, P.; Rieper, W.; Raue, R.; Kunde, K.; Aloys E. Azo Dyes. Ullmann's encycl. ind. chem. 2000, 1-93. https://doi.org/10.1002/14356007.a03_245
dc.relation.referencesen[25] Gung, B.W.; Taylor, R.T. Parallel Combinatorial Synthesis of Azo Dyes: A Combinatorial Experiment Suitable for Undergraduate Laboratories. J. Chem. Educ. 2004, 81, 1630-1632. https://doi.org/10.1021/ed081p1630
dc.relation.referencesen[26] Rydchuk, M.; Vrublevska T.; Boyko M.; Korkuna, O. Masking is the Effective Alternative to the Separation during Osmium Determination by Means of Azo Dyes in Complex Samples. Chem. Chem. Technol. 2010, 4, 115-124. https://doi.org/10.23939/chcht04.02.115
dc.relation.referencesen[27] Nadtoka, O. Nonlinear Optical Effects in Polymeric Azoesters. Chem. Chem. Technol. 2010, 4, 185-190. https://doi.org/10.23939/chcht04.03.185
dc.relation.referencesen[28] Naji, A.M.; Abdula, A.M.; Nief O.A.; Abdullah, E.K. Synthe-sis, Characterization, Antimicrobial and Molecular Docking Study of Benzooxadiazole Derivatives. Chem. Chem. Technol. 2022, 16, 25-33. https://doi.org/10.23939/chcht16.01.025
dc.relation.referencesen[29] Kulkarni, M.; Thakur, P. The Effect of UV/TiO2/H2O2 Process and Influence of Operational Parameters on Photocatalytic Degrada-tion of Azo Dye in Aqueous TiO2 Suspension. Chem. Chem. Tech-nol. 2010, 4, 265-270. https://doi.org/10.23939/chcht04.04.265
dc.relation.referencesen[30] Gilbert, A.M.; Failli, A.; Shumsky, J.; Yang, Y.; Severin, A.; Singh, G.; Hu, W.; Keeney, D.; Petersen, P.J.; Katz, A.H. Pyrazoli-dine-3,5-diones and 5-Hydroxy-1H-pyrazol-3(2H)-ones, Inhibitors of UDP-N-acetylenolpyruvyl Glucosamine Reductase. J. Med. Chem. 2006, 49, 6027-6036. https://doi.org/10.1021/jm060499t
dc.relation.referencesen[31] Hugo, I.; Funderburk, L.H. Process for the Preparation of 2,3,3-Trimethyl Indolenines, US3639420 A, Febuary 1, 1972.
dc.relation.referencesen[32] Piggott, H.A.; Hulme, Ch. Heterocyclic Nitrogen Compounds. US2016836, October 8, 1935.
dc.relation.referencesen[33] Lyubich, M.S.; Isaev, S.G.; Al'perovich, M.A.; Shpileva, I.S.; Arshava, B.M. Interaction of 5-Amino-2,3-trimethyl-3H-indole with p-Nitrobenzaldehyde. Chem. Heterocycl. Compd. 1984, 20, 976-977. https://doi.org/10.1007/BF00506391
dc.relation.referencesen[34] Bigelow, H.E.; Robinson, D.B. Azobenzene. Org. Synth. 1942, 22, 103. https://doi.org/10.15227/orgsyn.022.0028
dc.relation.referencesen[35] Bhatnagar, I; George M.V. Oxidation of Phenylhydrazones with Manganese Dioxide. J. Org. Chem. 1967, 32, 2252-2256. https://doi.org/10.1021/jo01282a036
dc.relation.urihttps://doi.org/10.48422/IMIST.PRSM/ajees-v3i3.9681
dc.relation.urihttps://doi.org/10.1016/j.jpowsour.2010.12.038
dc.relation.urihttps://doi.org/10.1016/j.optlastec.2011.12.019
dc.relation.urihttps://doi.org/10.1016/S1386-1425(99)00164-X
dc.relation.urihttps://doi.org/10.1038/srep03260
dc.relation.urihttps://doi.org/10.1016/j.saa.2014.02.118
dc.relation.urihttps://doi.org/10.1016/j.tetlet.2006.03.125
dc.relation.urihttps://doi.org/10.1016/j.jphotochem.2006.02.029
dc.relation.urihttps://doi.org/10.1016/j.saa.2014.01.113
dc.relation.urihttps://doi.org/10.1016/j.dyepig.2010.02.009
dc.relation.urihttps://doi.org/10.1016/j.dyepig.2010.07.008
dc.relation.urihttps://doi.org/10.1016/j.trac.2015.11.021
dc.relation.urihttps://doi.org/10.1038/ncomms11118
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dc.relation.urihttps://doi.org/10.1021/ma201014n
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dc.rights.holder© Національний університет “Львівська політехніка”, 2023
dc.rights.holder© Bukia T., Utiashvili M., Tsiskarishvili M., Jalalishvili S., Gogolashvili A., Tatrishvili T., Petriashvili G., 2023
dc.subjectазобарвники
dc.subjectбіс-азобарвник
dc.subjectвідновлення
dc.subject2
dc.subject3
dc.subject3-триметил-3Н-індоленін
dc.subjectсинтез
dc.subjectazo dyes
dc.subjectbis azo dye
dc.subjectreduction
dc.subject2
dc.subject3
dc.subject3-trimethyl-3H-indolenine
dc.subjectsynthesis
dc.titleSynthesis of Some Azo Dyes Based on 2,3,3-Trimethyl-3H-indolenine
dc.title.alternativeСинтез деяких азобарвників на основі 2,3,3 триметил 3H індоленіну
dc.typeArticle

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Chemistry & Chemical Technology. – 2023. – Vol. 17, No. 3