Study of environment and pH effects on the spectral behavior of arylazobenzylidene dyes


Journal: Vol.12, No.2, Spring 2018 - Article 1   Pages :  69 Until 78



Article Code:
PCCC-2017-12-20-372

Authors:
Ali Ghanadzadeh Gilani : University of Guilan - Department of Chemistry
A. Mohammadi: Faculty of Sciences, University of Guilan - Department of Chemistry
Mahshid Riazi: University of Guilan - Department of Chemistry


Article's abstract:

In this study, four arylazobenzylidene dyes a-d were synthesized with excellent yields in two steps using the Knoevenagel condensation and azo-coupling reactions. Absorption spectra of these dyes with different substituents were investigated in organic solvents as a function of solvent polarity. The spectral features of synthesized arylazobenzylidene dyes were described according to azo-hydrazone tautomerism as well as the solvatochromic characteristic of the approved tautomer. The nature and degree of solute-solvent interactions were illustrated using Kamlet-Taft multiparameter polarity scales. The effects of acid-base on the UV-visible absorption spectra of the dyes were reported. In addition, different absorption characteristics were observed for these dyes in pure diethanolamine.


Keywords:
Arylazobenzylidene dye, Solvatochromism, Tautomerism, Substituent effect

References:
1. Zollinger H 1991 In Color chemistry: syntheses, properties and application of organic dyes and pigments (Weinheim) 2. Freeman H S and Peters AT 2000 In Colorants for Non-Textile Applications (Amsterdam: Elsevier) 3. Christie R M 2001 In Colour Chemistry, Royal Society of Chemistry (Cambridge) 4. Griffiths J 1972 Chem. Soc. Rev. 1(1972) 481. 5. S.S. Razi, R. Ali, P. Srivastava, M. Shahid, A. Misra, RSC Adv. 4, (2014) 16999. 6. J.Y. Park, Y. Hirata, K. Hamada, Dyes Pigm. 95 (2012) 502. 7. D.H. Song, H.Y. Yoo, J.P. Kim, Dyes Pigm. 75 (2007) 727. 8. G.R.J.Y. Chang, D.G. Braun, J. Chromatogr. B: Biomed. Sci. App. 272 (1983) 21. 9. W. Huang, Y. Li, H. Lin, H. Lin, Spectrochim. Acta A 86 (2012) 437. 10. N. Hosain Nataj, E. Mohajerani, H. Nemati, A. Moheghi, M.R. Yazdanbakhsh, M. Goli, A. Mohammadi, J. Appl. Polym. Sci. 127 (2013) 456. 11. A.C. Razus, L. Birzan, M. Cristea, V. Tecuceanu, L. Blanariu, C. Enache, Dyes Pigm. 80 (2009) 337. 12. J. Xue, S. Wang, L. Zhang, X. Li, Dyes Pigm. 75 (2007) 369. 13. A. Mohammadi, M. Safarnejad, Spectrochim. Acta A 126 (2014) 105. 14. M.A. Rauf, S. Hisaindee, N. Saleh, RSC Adv. 5 (2015) 18097. 15. X.C. Chen, T. Tao, Y.G. Wang, Y.X. Peng, W. Huang, H.F. Qian, Dalton Trans. 41 (2012) 11107. 16. H.Y. Lee, X. Song, H. Park, M.H. Baik, D. Lee, J. Am. Chem. Soc. 132 (2010) 12133. 17. F. Ucun, A. Saglam, I. Kara, F. Karcı, J. Mol. Struct: THEOCHEM 868 (2008) 94. 18. Y.H. Ebead, Dyes Pigm. 92 (2011) 705. 19. C.N.R. Rao, S. Singh, V.P. Senthilnathan, Chem. Soc. Rev. 5 (1976) 297. 20. M.A. Kessler, O.S. Wolfbeis, Spectrochim. Acta A 47 (1991) 187. 21. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003. 22. A. Mohammadi, M.R. Yazdanbakhsh, L. Farahnak, Spectrochim. Acta A 89 (2012) 238. 23. M.R. Yazdanbakhsh, A. Mohammadi, J. Mol. Liq. 148 (2009) 35. 24. M. Kamlet, J. Abbound, R. Taft, In: Taft R (ed) An Examination of Linear Solvation Energy Relationships, In Progress in Physical Organic Chemistry, Wiley, New York, 1982. 25. M. Kamlet, J. Abbound, M. Abraham, R. Taft, J. Org. Chem. 48 (1983) 2877.


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