Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

2012
Authors
Alimmari, Adel SAMijin, Dušan

Vukicevic, Radovan
Božić, Bojan

Valentić, Nataša V.

Vitnik, Vesna

Vitnik, Željko

Ušćumlić, Gordana

Article (Published version)
Metadata
Show full item recordAbstract
Background: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. Results: The structure of the dyes was confirmed by UV-vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. Conclusions: The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.
Keywords:
Arylazo pyridone dyes / Tautomerism / Solvent effect / Substituent effect / DFT caculationSource:
Chemistry Central Journal, 2012, 6Publisher:
- BMC
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1186/1752-153X-6-71
ISSN: 1752-153X
PubMed: 22824496
WoS: 000313129700001
Scopus: 2-s2.0-84873927057
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IHTMTY - JOUR AU - Alimmari, Adel SA AU - Mijin, Dušan AU - Vukicevic, Radovan AU - Božić, Bojan AU - Valentić, Nataša V. AU - Vitnik, Vesna AU - Vitnik, Željko AU - Ušćumlić, Gordana PY - 2012 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1048 AB - Background: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. Results: The structure of the dyes was confirmed by UV-vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. Conclusions: The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data. PB - BMC T2 - Chemistry Central Journal T1 - Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes VL - 6 DO - 10.1186/1752-153X-6-71 ER -
@article{ author = "Alimmari, Adel SA and Mijin, Dušan and Vukicevic, Radovan and Božić, Bojan and Valentić, Nataša V. and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana", year = "2012", abstract = "Background: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. Results: The structure of the dyes was confirmed by UV-vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. Conclusions: The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.", publisher = "BMC", journal = "Chemistry Central Journal", title = "Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes", volume = "6", doi = "10.1186/1752-153X-6-71" }
Alimmari, A. S., Mijin, D., Vukicevic, R., Božić, B., Valentić, N. V., Vitnik, V., Vitnik, Ž.,& Ušćumlić, G.. (2012). Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes. in Chemistry Central Journal BMC., 6. https://doi.org/10.1186/1752-153X-6-71
Alimmari AS, Mijin D, Vukicevic R, Božić B, Valentić NV, Vitnik V, Vitnik Ž, Ušćumlić G. Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes. in Chemistry Central Journal. 2012;6. doi:10.1186/1752-153X-6-71 .
Alimmari, Adel SA, Mijin, Dušan, Vukicevic, Radovan, Božić, Bojan, Valentić, Nataša V., Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, "Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes" in Chemistry Central Journal, 6 (2012), https://doi.org/10.1186/1752-153X-6-71 . .