Solvatochromism, tautomerism and dichroism of some azoquinoline dyes in liquids and liquid crystals

Dyes and Pigments

Volumn 92, Issue 3, 2012, Pages 1320-1330

  Ghanadzadeh Gilani, A ^a,b   Moghadam, M ^a   Zakerhamidi, M S ^b   Moradi, E ^c  

^a UNIVERSITY OF GUILAN   (Iran)

^b UNIVERSITY OF TABRIZ   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Anisotropic host; Azo hydrazone tautomerism; Azoquinoline dye; Hetarylazoquinoline dye: solvatochromic method; Linear dichroism; Multiparameter polarity scale

Indexed keywords

ANISOTROPIC HOST; AZO/HYDRAZONE TAUTOMERISM; AZOQUINOLINE DYE; HETARYLAZOQUINOLINE DYE: SOLVATOCHROMIC METHOD; LINEAR DICHROISM; MULTIPARAMETERS;

ANISOTROPY; AZO DYES; EMISSION SPECTROSCOPY; LIQUID CRYSTALS; SOLVENTS;

DICHROISM;

EID: 80054057881     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.09.021     Document Type: Article

References (41)

1. H. Zollinger Color chemistry: syntheses, properties and application of organic dyes and pigments 2nd ed. 1991 VCH Weinheim
2. G. Pavlovic, L. Racane, H. Cicak, and V. Tralic-Kulenovic The synthesis and structural study of two benzothiazolyl azo dyes: X-ray crystallographic and computational study of azo-hydrazone tautomerism Dyes Pigments 83 2009 354 362
3. W. Huang Structural and computational studies of azo dyes in the hydrazone form having the same pyridine-2,6-dione component (II): C.I. Disperse Yellow 119 and C.I. Disperse Yellow 211 Dyes Pigments 79 2008 69 75
4. N. Ertan Synthesis of some hetarylazopyrazolone dyes and solvent effects on their absorption spectra Dye Pigments 44 2000 41 48
5. I. Sener, F. Karc, N. Ertan, and E. Klc Synthesis and investigations of the absorption spectra of hetarylazo disperse dyes derived from 2,4-quinolinediol Dye Pigments 70 2006 143 148 (Pubitemid 41644281)
6. F. Karc, and N. Ertan Visible absorption spectra of some novel heteroarylazo disperse dyes derived from 2-hydroxy-1,4-naphthoquinone Color Technol 121 2005 153 157 (Pubitemid 40875875)
7. F. Karc, and N. Ertan Hetarylazo disperse dyes derived from 3-methyl-1-(30,50-dipiperidino-s-triazinyl)-5-pyrazolone as coupling component Dye Pigments 55 2002 99 108 (Pubitemid 35374863)
8. F. Karc, and N. Ertan Synthesis of some novel hetarylazo disperse dyes derived from 4-hydroxy-2H-1-benzopyran-2-one (4-hydroxycoumarin) as coupling component and investigation of their absorption spectra Dye Pigments 64 2005 243 249 (Pubitemid 40058689)
9. A.S. Amin Determination of molybdenum in human urine by spectrophotometric method using thiazolylazo compounds as chromogenic reagents Anal Lett 32 1999 1575 1587 (Pubitemid 29275303)
10. I.S. Ahmed Selective spectrophotometric investigation and determination with some thiazolylazo compounds Instrum Sci Technol 33 2005 33 45
11. A.F. Shoair, A.A. El-Bindary, A.Z. El-Sonbati, and R.M. Younes Stereochemistry of new nitrogen containing heterocyclic aldehyde. VI. Novel structural and properties models of uranyl with quinoline azo dyes Spectrochim Acta A 57 2001 1683 1691 (Pubitemid 32544463)
12. A. Saylam, Z. Seferoglu, and N. Ertan Synthesis and spectroscopic properties of new hetarylazo 8-hydroxyquinolines from some heterocyclic amines Dyes Pigments 76 2008 470 476 (Pubitemid 47382557)
13. F. Karc, and F. Karc Synthesis of some novel pyrazolo[5,1-c][1,2,4] triazine derivatives and investigation of their absorption spectra Dyes Pigments 76 2008 97 103
14. A.S. Shawali, and M.A.N. Mosselhi Hydrazonoyl halides: useful building blocks for the synthesis of arylazoheterocycles J Heterocycl Chem 40 5 2003 725 746 (Pubitemid 37362919)
15. A.S. Shawali Synthesis and tautomerism of aryl- and hetaryl-azo derivatives of bi- and tri-heterocycles J Adv Res 1 2010 255 290
16. Y.H. Ebead, R.F. Fandy, S.E. Zayed, E. Abd-Elshafi, and S.A. Ibrahim Tautomeric structures of some 2-arylazo-1-hydroxycyclohex-1-en-3-one: Spectroscopic investigations and theoretical studies Can J Anal Sci Spect 53 2009 282 293
17. A. Ghanadzadeh Gilani, M.R. Yazdanbakhsh, N. Mahmoodi, M. Moghadam, and E. Moradi Solvatochromism and dichroism of fluorinated azoquinolin-8-ol dyes in liquid and liquid crystalline solutions J Mol Liq 139 2008 72 79
18. K. Wojciechowski, and A. Szymczak The research of the azo-hydrazone equilibrium by means of AM1 method based on the example of an azo dye-the Schaffer salt derivative Dyes Pigments 75 2007 45 51 (Pubitemid 46554997)
19. Vikman K. Studies on fastness properties of ink jet prints on coated papers. Doctoral dissertation, Helsinki University of Technology, Laboratory of Forest Products Chemistry, Finland; 2004.
20. 13C, N-H, H-H, C-H COSY, H-H NOESY NMR and UV-Vis studies of Solophenyl red 3BL dye azo-hydrazone tautomerism in various solvents Spectrochim Acta A 63 2006 247 254 (Pubitemid 43131467)
21. H. Joshi, F.S. Kamounah, C. Gooijer, G. van der Zwan, and L. Antonov Excited state intramolecular proton transfer in some tautomeric azo dyes and schiff bases containing an intramolecular hydrogen bond J Photochem Photobiol A 152 2002 183 191
22. P. Ball, and C.H. Nicholls Azo-hydrazone tautomerism of hydroxyazo compounds - a review Dyes Pigments 3 1982 5 26 (Pubitemid 12517365)
23. M. Dakiky, K. Kanan, and M. Khamis Aggregation of o, o′- dihydroxyazo dyes II. Interaction of 2-hydroxy-4-nitrophenylazoresorcinol in DMSO and DMF Dyes Pigments 41 1999 199 209
24. 1H NMR and steady-state fluorescence techniques Dyes Pigments 69 2006 93 101 (Pubitemid 41015403)
25. B.R. Hsieh, D. Desilets, and P.M. Kazmaier Azo-hydrazone tautomerism of an o, o'-dihydroxy azo dye-A spectroscopic study Dyes Pigments 14 1990 165 189
26. Q. Peng, M. Li, K. Gao, and L. Cheng Hydrazone-azo tautomerism of pyridone azo dyes. Part III-Effect of dye structure and solvents on the dissociation of pyridone azo dyes Dyes Pigments 18 1992 271 286 (Pubitemid 23589607)
27. C. Motoc, and G. Iacobescu Birefringence of azo dye doped nematic liquid crystals J Optoelectron Adv M 8 2006 295 298 (Pubitemid 43598279)
28. K. Ichimura Photoalignment of liquid-crystal systems Chem Rev 100 2000 1847 1873
29. X. Tong, and Y. Zhao Multiple photochemical processes in liquid crystalline azo dye-doped liquid crystals Chem Mater 21 2009 4047 4054
30. D.R.C. Matazo, R.A. Ando, A.C. Borin, and P.S. Santos Azo hydrazone tautomerism in protonated aminoazobenzenes: resonance raman spectroscopy and quantum-chemical calculations J Phys Chem A 112 2008 4437 4443
31. M.S. Masoud, A.E. Ali, M.A. Shaker, and M. Abdul Ghani Solvatochromic behavior of the electronic absorption spectra of some azo derivatives of amino pyridines Spectrochim Acta A 60 2004 3155 3159
32. A. Ghanadzadeh, M.A. Shahzamanian, S. Shoarinejad, M.S. Zakerhamidi, and M. Moghadam Guest-host interaction of some aminoazobenzene dyes doped in liquid crystalline matrix J Mol Liq 136 2007 22 28 (Pubitemid 47488528)
33. C. Reichardt Solvents and solvent effects in organic chemistry 2nd ed. 1988 Wiley-VCH
34. J. Michl, and E.W. Thulstrup Spectroscopy with polarized light 1995 Wiley-VCH Verlag GmbH
35. T. Aysha, S. Lunak, A. Lycka, and R. Hrdina Synthesis, absorption and fluorescence of hydrazone colorants based on pyrrolinone esters Dyes Pigments 91 2 2011 170 176
36. S. Stoyanov, and L. Antonov Quantitative analysis of azo-quinonehydrazone tautomeric equilibrium Dyes Pigments 10 1988 33 45
37. S. Stoyanov, L. Antonov, B. Soloveytchik, and V. Petrova Quantitative analysis of tautomeric equilibrium in 1-phenylazo4naphthols-a new approach Dyes Pigments 26 1994 149 158
38. R.D. Reeves, and K.S. Kaiser Selective solvation of hydrophobic ions in structured solvents. Azo-hydrazone tautomerism of azo dyes in aqueous organic solvents J Org Chem 35 1970 3670 3675
39. A.R. Katritzky, D.C. Fara, H. Yang, K. Tamm, T. Tamm, and M. Karelson Quantitative measures of solvent polarity Chem Rev 104 1 2004 175 198
40. D. Statman, and I. Jánossy Study of photoisomerization of azo dyes in liquid crystals J Chem Phys 118 7 2003 3222 3232
41. Ghanadzadeh A. Dielectric and electro-optical properties of some cyanobiphenyl liquid crystals. PhD thesis, Aston University, Birmingham, UK; 1995.