Study of Environment and pH Effects on the Spectral Behavior of Arylazobenzylidene Dyes

Journal: Vol.11, No.2, Spring 2018 - Article 1   Pages :  69 Until 78

Article Code:

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

Article's abstract:

In this study, four arylazobenzylidene dyes (a-d) were synthesized with excellent yields in two steps using 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 multi-parameter 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. H. Yousefpour Navid, K. Gharanjig, M. Arami, Synthesis, Characterization and Textile Application of Novel Disperse Dyes, Prog. Color Colorants Coat., 7(2014), 155-163. 2. A. Mohammadi, B. Khalili, M. Tahavor, Novel push-pull heterocyclic azo disperse dyes containing piperazine moiety: Synthesis, spectral properties, antioxidant activity and dyeing performance on polyester fibers, Spectrochim. Acta A, 150(2015), 799-805. 3. A. Mohammadi, Z. Dehghan, M. Rassa, N. Chaibakhsh, Colorimetric probes based on bioactive organic dyes for selective sensing of cyanide and fluoride ions, Sens. Actuators B, 230(2016), 388-397. 4. P. Alaei, Sh. Rouhani, K. Gharanjig, A Dual Colorimetric and Fluorometric Anion Sensor Based on Polymerizable 1, 8-Naphthalimide Dye, Prog. Color Colorants Coat., 6(2013), 87-96. 5. A. Soleimani Gorgani, M. Jalili, Ink-Jet Printing of Cotton with Cationic Reactive Dye Based Inks, Prog. Color Colorants Coat., 6(2013), 1-8. 6. H. S. Freeman, A. T. Peters (Eds.), Colorants for Non-Textile Applications, Elsevier, 2000, 1-34. 7. D. H. Song, H. Y. Yoo, J. P. Kim, Synthesis of stilbene-based azo dyes and application for dichroic materials in poly(vinyl alcohol) polarizing films, Dyes Pigments, 75(2007), 727-731. 8. D. M. Marmion, Handbook of US. Colorants, third ed., John Wiley and Sons, Inc., New York, 1991. 9. S. M. T. Shaikh, J. Seetharamappa, P. B. Kandagal, D. H. Manjunatha, S. Ashoka, Spectroscopic investigations on the mechanism of interaction of bioactive dye with bovine serum albumin, Dyes Pigments, 74(2007), 665-671. 10. S. S. Razi, R. Ali, P. Srivastava, M. Shahid, A. Misra, An azo based colorimetric probe for the detection of cysteine and lysine amino acids and its real application in human blood plasma, RSC Adv., 4(2014), 16999-17007. 11. G. Sudesh Kumar and D. C. Neckers, Photochemistry of azobenzene-containing polymers, Chem. Rev., 89(1989), 1915-1925. 12. N. Hosain Nataj, E. Mohajerani, H. Nemati, A. Moheghi, M. R. Yazdanbakhsh, M. Goli, A. Mohammadi, Studying optical and nonlinear optical properties of synthesized azo dyes doped in polymer and liquid crystal using birefringence and Z-scan techniques, J. Appl. Polym. Sci., 127(2013), 456-462. 13. A. C. Razus, L. Birzan, M. Cristea, V. Tecuceanu, L. Blanariu, C. Enache, Novel mono- and bis-azo dyes containing the azulen-1-yl moiety: Synthesis, characterization, electronic spectra and basicity, Dyes Pigments, 80(2009), 337-342. 14. J. Xue, S. Wang, L. Zhang, X. Li, Study on the synthesis and photoconductivity of bisazo compounds having 1,3,4-oxadiazole, Dyes Pigments, 75(2007), 369-372. 15. A. Mohammadi, M. Safarnejad, Synthesis, structural characterization and tautomeric properties of some novel bis-azo dyes derived from 5-arylidene-2,4-thiazolidinone, Spectrochim. Acta A, 126(2014), 105-111. 16. M.A. Rauf, S. Hisaindee, N. Saleh, Spectroscopic studies of keto-enol tautomeric equilibrium of azo dyes, RSC Adv., 5(2015), 18097-18110. 17. X. C. Chen, T. Tao, Y. G. Wang, Y.X. Peng, W. Huang, H. F. Qian, Azo-hydrazone tautomerism observed from UV-vis spectra by pH control and metal-ion complexation for two heterocyclic disperse yellow dyes, Dalton Trans., 41(2012), 11107-11115. 18. H. Y. Lee, X. Song, H. Park, M.H. Baik, D. Lee, Torsionally Responsive C3-Symmetric Azo Dyes: Azo−Hydrazone Tautomerism, Conformational Switching, and Application for Chemical Sensing, J. Am. Chem. Soc., 132(2010), 12133-12144. 19. A. Ghanadzadeh Gilani, E. Moradi, S. Binay, M. Moghadam, Tautomeric behavior of some azoquinoline dyes in liquid and liquid crystalline media, Spectrochim. Acta A, 87(2012), 112-118. 20. Y. H. Ebead, Spectrophotometric investigations and computational calculations of prototropic tautomerism and acid–base properties of some new azo dyes, Dyes Pigments, 92(2011), 705-713. 21. C. N. R. Rao, S. Singh, V. P. Senthilnathan, Spectroscopic studies of solute-solvent interactions, Chem. Soc. Rev., 5(1976), 297-316. 22. A. Ghanadzadeh Gilani, M. R. Yazdanbakhsh, N. Mahmoodi, M. Moghadam, E. Moradi, Solvatochromism and dichroism of fluorinated azoquinolin-8-ol dyes in liquid and liquid crystalline solutions, J. Mol. Liq., 139(2008), 72-79. 23. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003. 24. A. Mohammadi, M. R. Yazdanbakhsh, L. Farahnak, Synthesis and evaluation of changes induced by solvent and substituent in electronic absorption spectra of some azo disperse dyes, Spectrochim. Acta A, 89(2012), 238-242. 25. A. Alimmari, D. Mijin, R. Vukićević, B. Božić, N. Valentić, V. Vitnik, Ž. Vitnik, G. Ušćumlić, Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes, Chem. Cent. J., 6(2012), 71-78. 26. M. R. Yazdanbakhsh, A. Mohammadi, Synthesis, substituent effects and solvatochromic properties of some disperse azo dyes derived from N-phenyl-2, 2′-iminodiethanol, J. Mol. Liq., 148(2009), 35-39. 27. Q. Peng, M. Li, K. Gao, L. Cheng, Hydrazone-azo tautomerism of pyridine azo dyes. Part III. Effect of dye structure and solvent on the dissociation of pyridone azo dyes, Dyes Pigments, 18(1992), 271-286. 28. F. Karci, F. Karci, Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives, Dyes Pigments, 76(2008), 147-157. 29. M. Khattab, M. V. Dongen, F. Wang, A. H. A. Clayton, Solvatochromism and linear solvation energy relationship of the kinase inhibitor SKF86002, Spectrochim. Acta A, 170(2017), 226-233. M. Kamlet, J. Abboud, M. Abraham, R. Taft, Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, .pi.*, .alpha., and beta., and some methods for simplifying the generalized solvatochromic equation, J. Org. Chem., 48(1983), 2877-2887.

Article's file
Page view: 985
Article's download quantity : 13

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:986
Online Visitors:62