Synthesis and characterization of novel yellow azo dyes from 2-morpholin-4-yl-1,3-thiazol-4(5H)-one and study of their azo-hydrazone tautomerism

Dyes and Pigments

Volumn 99, Issue 2, 2013, Pages 291-298

  Umape, Prashant G ^a   Patil, Vikas S ^a   Padalkar, Vikas S ^a   Phatangare, Kiran R ^a   Gupta, Vinod D ^a   Thate, Abhinav B ^a   Sekar, Nagaiyan ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2 (Morpholin 4 yl) 13 thiazol 4(5H) one; Azo hydrazone tautomerism; Density functional theory; Diazocoupling; Diazotization; Yellow azo dyes

Indexed keywords

2-(MORPHOLIN-4-YL)-13-THIAZOL-4(5H)-ONE; AZO-HYDRAZONE TAUTOMERISM; DIAZOCOUPLING; DIAZOTIZATION; HYDRAZONE TAUTOMERIC FORM; PHOTOPHYSICAL PROPERTIES; SYNTHESIS AND CHARACTERIZATIONS; UV VISIBLE SPECTROSCOPY;

DENSITY FUNCTIONAL THEORY; OPTIMIZATION; THERMODYNAMIC STABILITY; THERMOGRAVIMETRIC ANALYSIS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

AZO DYES;

EID: 84879496530     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.05.002     Document Type: Article

References (30)

1. J. Koh, and A.J. Greaves Synthesis and application of an alkali-clearable azo disperse dye containing a fluorosulfonyl group and analysis of its alkali-hydrolysiskinetics Dyes and Pigments 50 2001 117 126 (Pubitemid 32752984)
2. R. Vijayaraghavan, N. Vedaraman, M. Surianarayanan, and D.R. MacFarlane Extraction and recovery of azo dyes into an ionic liquid Talanta 69 5 2006 1059 1062 (Pubitemid 43866165)
3. S. Machida, M. Araki, and K. Matsuo Studies of the water-soluble polymers. XVI. Azo dyes of poly-N-vinylimidazole Journal of Applied Polymer Science 12 2 1968 325 332
4. W.G. George Dyes and liquid crystals Dyes and Pigments 3 1982 203 209
5. K. Nejati, Z. Rezvani, and M. Seyedahmadian The synthesis, characterization, thermal and optical properties of copper, nickel, and vanadyl complexes derived from azo dyes Dyes and Pigments 83 2009 304 311
6. 2 oxidant of C.I. disperse yellow 79 Dyes and Pigments 91 2011 105 111
7. M.A. Metwally, E. Abdel-latif, F.A. Amer, and G. Kaupp Synthesis of new 5-thiazolyl azo-disperse dyes for dyeing polyester fabrics Dyes and Pigments 60 2004 249 264 (Pubitemid 37458247)
8. V. Mishra, and M.C. Jain 2-Amino-4-phenl-5-phenylazothiazole as an analytical reagent for spectrophotometric determination of iron (III) Journal of the Indian Chemical Society 65 1988 883 884
9. A.O. Abdelhamid, A.R. Sayed, and Y.H. Zaki Reaction of hydrazonoyl halides 511: a facile synthesis of 5-arylthiazoles and triazolino[4,3-a] pyrimidines as antimicrobial agents Phosphorus, Sulfur, and Silicon 182 2007 1447 1457
10. A.O. Abdelhamid, and A.R. Sayed Reaction of hydrazonoyl halides 52:1 synthesis and antimicrobial activity of some new pyrazolines and 1,3,4-thiadiazolines Phosphorus, Sulfur, and Silicon 182 2007 1767 1777
11. A.O. Abdelhamid, Z.H. Ismail, M.S. El Gendy, and M.M. Ghorab Reactions with hydrazonoyl halides 53:1 synthesis and antimicrobial activity of triazolino[4,3-a]pyrimidines and 5-arylazothiazoles Phosphorus, Sulfur, and Silicon 182 2007 2409 2418
12. A.M. Khalil, M.A. Berghot, M.A. Gouda, and S.A. El Bialy Synthesis and antibacterial studies of azodispersed dyes derived from 2-(thiazol-2-yl) phthalazine-1,4-diones Monatshefte für Chemie 141 2010 1353 1360
13. P. Ball, and C.H. Nichollst Azo-hydrazone tautomerism of hydroxyazo compounds - a review Dyes and Pigments 3 1982 5 26 (Pubitemid 12517365)
14. Y.D. Kim, J.H. Cho, C.R. Park, J. Choi, C. Yoon, and J.P. Kim Synthesis, application and investigation of structure-thermal stability relationships of thermally stable water-soluble azo naphthalene dyes for LCD red color filters Dyes and Pigments 89 2011 1 8
15. J. Farrera, I. Canal, P. Hidalgo-Fernandez, M.L. Perez-Garcia, O. Huertas, and F.J. Luque Towards a tunable tautomeric switch in azobenzene biomimetics: implications for the binding affinity of 2-(4′- hydroxyphenylazo)benzoic acid to streptavidin Chemistry - A European Journal 14 2008 2277 2285
16. H.Y. Lee, X. Song, H. Park, M. Baik, and D. Lee Torsionally responsive C3-symmetric azo dyes: azo-hydrazone tautomerism, conformational switching, and application for chemical sensing Journal of the American Chemical Society 132 2010 12133 12144
17. Y. Zhi-Gang, Z. Chun-Xia, Z. De-Feng, H.S. Freeman, C. Pei-Tong, and H. Jie Monoazo dyes based on 5,10-dihydrophenophosphazine, part 2: azo acid dyes Dyes and Pigments 81 2009 137 143
18. 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 and Pigments 83 2009 354 362
19. J. Griffiths, and W.J. Lee Synthesis, light absorption and fluorescence properties of new thiazole analogues of the xanthene dyes Dyes and Pigments 57 2003 107 114 (Pubitemid 36536887)
20. M. Kodomari, M. Suzuki, K. Tanigawaa, and T. Aoyama A convenient and efficient method for the synthesis of mono and N, N-disubstituted thioureas Tetrahedron Letters 46 2005 5841 5843 (Pubitemid 41078734)
21. V.H. Hartman, and R. Inge Darstellung und Charakterisierung 1,l-disubstituierter Thioharnstoffe Journal für Praktische Chemie 315 1973 143 148
22. 1H NMR and steady-state fluorescence techniques Dyes and Pigments 69 2006 93 101 (Pubitemid 41015403)
23. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09, revision C.01 2010 Gaussian, Inc Wallingford CT
24. O. Treutler, and R. Ahlrichs Efficient molecular numerical integration schemes Journal of Chemical Physics 102 1995 346 354
25. A.D. Becke A new mixing of Hartree-Fock and local density-functional theories Journal of Chemical Physics 98 1993 1372 1377
26. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Physical Review B 37 1988 785 789
27. W.J. Hehre, L. Radom, Pv.R. Schleyer, and J.A. Pople Ab initio molecular orbital theory 1986 Wiley New York
28. R. Bauernschmitt, and R. Ahlrichs Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory Chemical Physics Letters 256 1996 454 464 (Pubitemid 126160745)
29. F. Furche, and D. Rappaport Density functional theory for excited states: equilibrium structure and electronic spectra M. Olivucci, Computational photochemistry 2005 Elsevier Amsterdam 16 [Chapter 3]
30. Y.H. Ebead Spectrophotometric investigations and computational calculations of prototropic tautomerism and acid-base properties of some new azo dyes Dyes and Pigments 92 2011 705 713