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:

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.

Arylazobenzylidene dye, Solvatochromism, Tautomerism, Substituent effect

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.

Article's file
Page view: 265
Article's download quantity : 8

Article System Login

Prof. Zahra Ranjbar
Dr. Farahnaz Nourmohammadian
Assistant Editor:
Dr. Mozhgan Hosseinnezhad
ISSN (online):
Institute for Color Science and Technology (ICST)

Quick Access
What is your opinion about the manuscript subscription system of PCCC website?
Website Statistics
Page view:266
Online Visitors:10