1. JCCT
  2. Всі випуски
  3. Випуск 17, Номер 3, 2023
  4. Синтез деяких азобарвників на основі 2,3,3 триметил 3h індоленіну

Синтез деяких азобарвників на основі 2,3,3 триметил 3h індоленіну

JCCT.
2023;
Випуск 17, Номер 3
: cc. 549 - 556
https://doi.org/10.23939/chcht17.03.549
Автори:
  1. Tinatin Bukia
  2. Mariam Utiashvili
  3. Manana Tsiskarishvili
  4. Sopo Jalalishvili
  5. Ana Gogolashvili
  6. Tamara Tatrishvili
  7. Gia Petriashvili
1
Vladimir Chavchanidze Institute of Cybernetics of the Georgian Technical University
2
San Diego State University - Georgia
3
San Diego State University - Georgia
4
San Diego State University - Georgia
5
San Diego State University - Georgia
6
Iv. Javakhishvili Tbilisi State University, 2 Institute of Macromolecular Chemistry and Polymeric Materials, Iv. Javakhishvili Tbilisi State University
7
Vladimir Chavchanidze Institute of Cybernetics of the Georgian Technical University

Нові азосполуки на основі 2,3,3-три¬метил-3Н-індоленіну синтезовано й охарактеризовано за допомогою ІЧ-, ЯМР- і мас-спектрального аналізу. Синтез проводили трьома різними маршрутами: 1) відновленням ніт¬ро¬сполуки за допомогою Zn/NaOH у спирті; 2) нагрі¬ванням 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 від¬повідною азоскладовою.

азобарвники
біс-азобарвник
редукція
2,3,3-триметил-3Н-індоленін
синтез
  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
  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
  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
  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
  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
  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
  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
  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
  9. [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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  27. Nadtoka, O. Nonlinear Optical Effects in Polymeric Azoesters. Chem. Chem. Technol. 2010, 4, 185-190. https://doi.org/10.23939/chcht04.03.185
  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
  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
  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
  31. Hugo, I.; Funderburk, L.H. Process for the Preparation of 2,3,3-Trimethyl Indolenines, US3639420 A, Febuary 1, 1972.
  32. Piggott, H.A.; Hulme, Ch. Heterocyclic Nitrogen Compounds. US2016836, October 8, 1935.
  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
  34. Bigelow, H.E.; Robinson, D.B. Azobenzene. Org. Synth. 1942, 22, 103. https://doi.org/10.15227/orgsyn.022.0028
  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