Photo-oxidation of phenylazonaphthol dyes and their reactivity analysis in the gas phase and adsorbed on cellulose fibers states using DFT and TD-DFT

Dyes and Pigments

Volumn 89, Issue 1, 2011, Pages 16-22

  Zanjanchi, Farzaneh ^a   Hadipour, Nasser L ^a   Sabzyan, Hassan ^b   Beheshtian, Javad ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

^b UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Cycloaddition reaction; Ene reaction; Fading; Frontier molecular orbital theory; Photo decomposition; Singlet molecular oxygen

Indexed keywords

CYCLOADDITION REACTION; ENE REACTION; FADING; FRONTIER MOLECULAR ORBITALS; PHOTO-DECOMPOSITION; SINGLET MOLECULAR OXYGEN;

ADSORPTION; AZO DYES; CELLULOSE; CYCLOADDITION; MOLECULAR MODELING; MOLECULAR ORBITALS; ORBITS; OXIDATION; PHENOLS; SULFUR COMPOUNDS;

MOLECULAR OXYGEN;

EID: 78649322304     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2010.08.009     Document Type: Article

References (34)

1. N. Kuramato A.T. Peter, H.S. Freeman, Physico-Chemical principle of color chemistry 1996 Blackie London
2. J. Oakes Photofading of textile dyes Review of Progress in Coloration and Related Topics 2001 21 28
3. S.N. Batchelor, D. Carr, C.E. Coleman, L. Fairclough, and A. Jarvis The photofading mechanism of commercial reactive dyes on cotton Dyes and Pigments 59 2003 269 275
4. F. Wilkinson, W.P. Helman, and A.B. Ross Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution Journal Physical And Chemical Reference Data 22 1993 113 117
5. T. Hihara, Y. Okada, and Z. Morita Reactivity of phenylazonaphthol sulfonates, their estimation by semiempirical molecular orbital PM5 method, and the relation between their reactivity and azo-hydrazone tautomerism Dyes and Pigments 59 2003 201 222
6. I. Flemming Frontier orbitals and organic chemical reactions 1976 Wiley-Interscience Chichester
7. A. Rauk Orbital interaction theory of organic chemistry 2nd ed 2001 Wiley-Interscience New York
8. T. Hihara, Y. Okada, and Z. Morita Azo-hydrazone tautomerism of phenylazo-naphthol sulfonates and their analysis using semiempirical molecular orbital PM5 method Dyes and Pigments 59 1 2003 25 41
9. Zanjanchi F, Hadipour N, Sabzyan H, Beheshtian J. Journal of Physical Organic Chemistry, submitted for publication.
10. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheesemann 1998 Gaussian, Inc Pittsburgh (PA)
11. M. Karelson, and V.S. Lobanov Quantum-chemical descriptors in QSAR/Qspr studies Chemical Reviews 96 1996 1027 1043
12. R. Anantharaj, and T. Banerjee Evaluation and comparison of global scalar properties for the simultaneous interaction of ionic liquids with thiophene and pyridine Fluid Phase Equilibria 293 2010 22 31
13. R.K. Roy, S. Krishnamurti, P. Geerlings, and S. Pal Local softness and hardness based reactivity descriptors for predicting intra- and intermolecular reactivity sequences: carbonyl compounds The Journal of Physical Chemistry A 102 21 1998 3746 3755
14. R.G. Pearson, and W.E. Palke Support for a principle of maximum hardness The Journal of Physical Chemistry 96 8 1992 3283 3285
15. R.G. Parr, V.L. Szentpály, and S.B. Liu Electrophilicity index Journal of the American Chemical Society 121 1999 1922 1924
16. L.R. Domingo, J.A. Sáez, and P. Pérez A comparative analysis of the electrophilicity of organic molecules between the computed IPs and EAs and the HOMO and LUMO energies Chemical Physics Letters 438 2007 341 345
17. L.M.G. Jansen, I.P. Wilkes, F. Wilkinson, and D.R. Worrall The role of singlet molecular oxygen in the photodegradation of 1-arylazo-2-naphthols in methanol and on cotton Journal of Photochemistry and Photobiology A: Chemistry 125 1999 99 106
18. T. Hihara, Y. Okada, and Z. Morita Photo-oxidation of pyrazolinylazo dyes and an analysis of their reactivity as azo and hydrazone tautomers using the semiempirical molecular orbital PM5 method Dyes and Pigments 69 2 2006 151 176
19. T. Hihara, Y. Okada, and Z. Morita A semiempirical molecular orbital study on the photo-reactivity of monoazo reactive dyes derived from g- and J-acids Dyes and Pigments 73 2 2007 141 161
20. J. Bird, N. Brough, S. Dixon, and S.N. Batchelor Understanding adsorption phenomena: Investigation of the dye-cellulose interaction The Journal of Physical Chemistry B 110 2006 19557 19561
21. M.M. Dávila Jiménez, M.P. Elizalde González, and A.A. Peláez Cid Adsorption interaction between natural adsorbents and textile dyes in aqueous solution Colloids and Surfaces A: Physicochemical and Engineering Aspects 254 2005 107 114
22. A. Pielesz Spectroscopic study of interactions between model direct dyes and cotton Journal of Applied Polymer Science 104 2007 758 766
23. A. Pielesz, A. Wesełucha Birczyńska, H.S. Freeman, and A. Włochowicz Characterizing of model direct dyes interactions with cotton cellulose via 1D and 2D raman spectroscopy Cellulose 12 2005 497 506
24. L.C. Abbott, S.N. Batchelor, L. Jansen, J. Oakes, J.R. Lindsay Smith, and J.N. Moore Spectroscopic studies of Direct Blue 1 in solution and on cellulose surfaces: effects of environment on a bis-azo dye New Journal of Chemistry 28 2004 815 821
25. K. Fukui, H. Fujimoto, Frontier orbitals and reaction paths (selected papers of K. Fukui) World Scientific Series in 20th Century Chemistry vol. 7 1997 World Scientific Singapore
26. 4/peroxymonosulfate system: kinetics and mechanism study using Acid Orange 7 as a model compound Applied Catalysis B: Environmental 80 2008 116 121
27. T. Hihara, Y. Okada, and Z. Morita The photo-oxidation of reactive azobenzene dyes and an analysis of their reactivity for the azo and hydrazone tautomers using the semiempirical molecular orbital PM5 method Dyes and Pigments 75 2007 225 245
28. C. Skew, P. Kang, S. Khan, and C.S. Foote Low-temperature photosensitized oxidation of a guanosine derivative Journal of the American Chemistry Society 124 15 2002 3905 3913
29. Z. Morita, and S. Hada A semiempirical molecular orbital study on the reaction of an aminopyrazolinyl azo dye with singlet molecular oxygen Dyes and Pigments 41 1 1999 1 10
30. A.G. Griesbeck, T.T. El-Idreesy, W. Adam, and O. Krebs Ene-reactions with singlet oxygen W.M. Horspool, F. Lenci, 2nd ed CRC handbook of organic photochemistry and photobiology vol. 8 2003 CRC Press Boca Raton p. 1-20 [chapter 8].
31. P. Gilli, V. Bertolasi, L. Pretto, L. Antonov, and G. Gilli Variable-temperature x-ray crystallographic and DFT computational study of the N-H···O/N···H-O tautomeric competition in 1-(arylazo)-2-naphthols. Outline of a transition-state hydrogen-bond theory Journal of the American Chemistry Society 127 2005 4943 4953
32. W.M.F. Fabian, L. Antonov, D. Nedeltcheva, F.S. Kamounah, and P.J. Taylor Tautomerism in hydroxynaphthaldehyde anils and azo analogues: a combined experimental and computational study The Journal of Physical Chemistry A 108 2004 7603 7612
33. J. Griffiths, and C. Hawkins The photochemical oxidation of 4-arylazo-1-naphthols Journal of the Chemical Society, Chemical Communication 1972 463 464
34. J. Griffiths, and C. Hawkins Oxidation by singlet oxygen of arylazonaphthols exhibiting azo-hydrazone tautomerism Journal of the Chemical Society. Perkin Transactions 2 1977 747 752