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

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• 作者：Adel Alimmari (1)
  Du?an Mijin (1)
  Radovan Vuki?evi? (1)
  Bojan Bo?i? (1)
  Nata?a Valenti? (1)
  Vesna Vitnik (2)
  ?eljko Vitnik (3)
  Gordana U??umli? (1)
  
• 关键词：Arylazo pyridone dyes ; Tautomerism ; Solvent effect ; Substituent effect ; DFT caculation
• 刊名：Chemistry Central Journal
• 出版年：2012
• 出版时间：December 2012
• 年：2012
• 卷：6
• 期：1
• 全文大小：389KB
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• 作者单位：Adel Alimmari (1)
  Du?an Mijin (1)
  Radovan Vuki?evi? (1)
  Bojan Bo?i? (1)
  Nata?a Valenti? (1)
  Vesna Vitnik (2)
  ?eljko Vitnik (3)
  Gordana U??umli? (1)
  
  1. Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P.O. Box 3503, 11120, Belgrade, Serbia
  2. Department of Chemistry, ICTM, University of Belgrade, Studentski trg 12-16, 11000, Belgrade, Serbia
  3. Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000, Belgrade, Serbia
  
• ISSN：1752-153X

文摘

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, 1H NMR and 13C 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.