A novel barbituric acid-based azo dye and its derived polyamides: Synthesis, spectroscopic investigation and computational calculations

Dyes and Pigments

Volumn 95, Issue 3, 2012, Pages 587-599

  Zamanloo, Mohammad Reza ^a   Shamkhali, Amir Nasser ^a   Alizadeh, Masoumeh ^a   Mansoori, Yagoub ^a   Imanzadeh, Golamhassan ^a  

^a UNIVERSITY OF MOHAGHEGH ARDABILI   (Iran)

Author keywords

Azo dye; Barbituric acid; Computational calculations; Polyamides; Tautomerism; UV vis spectroscopy

Indexed keywords

BARBITURIC ACID; BASIS SETS; COMPUTATIONAL CALCULATIONS; GASPHASE; HOMO-LUMO ENERGIES; IR AND UV-VIS SPECTROSCOPIES; POLARIZABLE CONTINUUM MODEL; SOLVATION EFFECT; SPECTROSCOPIC INVESTIGATIONS; STRUCTURAL FEATURE; TAUTOMERIC FORMS; TAUTOMERISM; UV-VIS ABSORPTION SPECTROSCOPY; UV-VIS SPECTROSCOPY; XRD TECHNIQUE;

ABSORPTION SPECTROSCOPY; AMIDES; CONTINUUM MECHANICS; DENSITY FUNCTIONAL THEORY; ELECTROMAGNETIC WAVE ABSORPTION; ORGANIC SOLVENTS; PH EFFECTS; POLYAMIDES; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY; ULTRAVIOLET VISIBLE SPECTROSCOPY; VISCOSITY MEASUREMENT;

AZO DYES;

EID: 84864091164     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.05.028     Document Type: Article

References (56)

1. H. Zollinger Color chemistry 3th ed. 2003 Verlag Helvetica Chimica Acta Switzerland
2. C.R. Moylan, B.J. McNelis, L.C. Nathan, M.A. Marques, E.L. Hermstad, and B.A. Brichler Challenging the auxiliary donor effect on molecular hyperpolarizability in thiophene-containing nonlinear chromophores: X-ray crystallographic and optical measurements on two new isomeric chromophores J Org Chem 69 2004 8239 8243
3. M.M.M. Raposo, A.M.R.C. Sousa, A.M.C. Fonseca, and G. Kirsch Thienylpyrrole azo dyes: synthesis, solvatochromic and electrochemical properties Tetrahedron 61 2005 8249 8256
4. A.S. Abd-El-Aziz, P.O. Shipman, P.R. Shipley, B.N. Boden, S. Aly, and P.D. Harvey Homo- and Co-polymers of norbornene containing aryl- and hetaryl-azo dyes; synthesis and sensing properties Macromol Chem Phys 210 2010 2099 2106
5. F. Karci Synthesis of disazo dyes derived from heterocyclic components Color Technol 121 2005 275 280
6. M. He, Y. Zhou, R. Liu, J. Dia, Y. Cui, and T. Zhang Novel nonlinearity-transparency thermal stability trade-off of thiazolylazopyrimidine chromophores for nonlinear optical application Dyes Pigments 80 2009 6 10
7. M.S. Masoud, A.E. Ali, M.A. Shaker, and M.A. Ghani Solvatochromic behavior of the electronic absorption spectra of some azo derivatives of amino pyridines Spectrochim Acta A Mol Biomol Spectrosc 60 2004 3155 3159
8. R.M.F. Batista, S.P.G. Costa, M. Belsley, and M.M.M. Raposo Synthesis and second-order nonlinear optical properties of new chromophores containing benzimidazole, thiophene, and pyrrole heterocycles Tetrahedron 63 2007 9842 9849
9. M.M.M. Raposo, A.M.F.P. Ferreira, M. Amaro, M. Belsley, and J.C.V.P. Moura The synthesis and characterization of heterocyclic azo dyes derived from 5-N, N-dialkylamino-2,2'-bithiophene couplers Dyes Pigments 83 2009 59 65
10. A.M. Zhong, Y.M. Zhou, and F.X. Qiu Synthesis and characterization of thiazole chromophores with high second-order polarizability Acta Chim Sinica 64 2006 343 347
11. T. Konstantinov, and P. Petrov On the synthesis of some bifunctional reactive triazine dyes Dyes Pigments 52 2 2002 115 120
12. P.J. Coelho, L.M. Carvalho, J.C.V.P. Moura, and M.M.M. Raposo Novel photochromic 2,2′-bithiophene azo dyes Dyes Pigments 82 2009 130 133
13. M.S. Sujamol, C.J. Athira, Y. Sindhu, and K. Mohanan Synthesis, spectroscopic characterization, electrochemical behaviour and thermal decomposition studies of some transition metal complexes with an azo derivative Spectrochim Acta A Mol Biomol Spectrosc 75 2010 106 112
14. L.J. Chen, Y.J. Cui, G.D. Qian, and M.Q. Wang Synthesis and spectroscopic characterization of an alkoxysilane dye containing azo-benzothiazole chromophore for nonlinear optical applications Dyes Pigments 73 2007 338 343
15. R.M.F. Batista, S.P.G. Costa, E.L. Malheiro, M. Belsley, and M.M.M. Raposo Synthesis and characterization of new thienylpyrrolylbenzothiazoles as efficient and thermally stable nonlinear optical chromophores Tetrahedron 63 2007 4258 4265
16. Q.W. Pan, Z.Y. Zhang, C.S. Fang, S. Wei, Q.T. Gu, and X.W. Wu Synthesis and characterization of thiazolylazo chromophore for nonlinear optical applications Mater Lett 50 2001 284 286
17. L. Qiu, Y.Q. Shen, J.M. Hao, J.F. Zhai, F.H. Zu, and T. Zhang Study on novel second-order NLO azo-based chromophores containing strong electron-withdrawing groups and different conjugated bridges J Mater Sci 39 2004 2335 2340
18. C.W. Dirk, H.E. Katz, and M.L. Schilling Use of thiazole rings to enhance molecular second-order nonlinear optical susceptibilities Chem Mater 2 1990 700 705
19. P. Hrobarik, I. Sigmundova, and P. Zahradnk Preparation of novel push-pull benzothiazole derivatives with reverse polarity: compounds with potential non-linear optic application Synthesis 4 2005 600 604
20. M. Lorenz, and K.H. Schuendehuette Derivatives of azobarbituric acid or salts or complexes thereof US4,628,082 1986
21. R.Y. Levina, and F.K. Velichko Advances in the chemistry of barbituric acids Russ Chem 29 1960 437 459
22. F. Karci, and F. Karci The synthesis and solvatochromic properties of some novel heterocyclic disazo dyes derived from barbituric acid Dyes Pigments 77 2008 451 456
23. F. Ucun, A. Saglam, I. Kara, and F. Karci Investigation of ground state tautomeric form of a heterocyclic disazo dye derived from barbituric acid by ab initio Hartree-Fock and density functional theory calculations J Mol Struct Theochem 868 2008 94 100
24. A.H. Amrallah, N.A. Abdalla, and E.Y. El-Haty Spectrophotometric studies on some Arylazo barbituric acids and Arylazo pyrimidine in organic solvents and in buffer solutions J Chin Chem Soc 54 2007 1629 1637
25. R. Gup, E. Giziroglu, and B. Kirkan Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline Dyes Pigments 73 2007 40 46
26. C.J. Barrett, J. Mamiya, K.G. Yager, and T. Ikeda Photo-mechanical effects in azobenzene-containing soft materials Soft Matter 3 2007 1249 1261
27. K.G. Yager, and C.J. Barrett Novel photo-switching using azobenzene functional materials J Photoch Photobio A 182 2006 250 261
28. P.P. Kasture, Y.A. Sonawane, R.N. Rajule, and G.S. Shankarling Synthesis and characterisation of benzothiazole-based solid-state fluorescent azo dyes Color Technol 126 2010 248 252
29. C.C. Tsai, T.Y. Chao, H.L. Lin, Y.H. Liu, H.L. Chang, and Y.L. Liu The facile synthesis and optical nonlinearity of hyperbranched polyaspartimides with azobenzene dyes Dyes Pigments 82 2009 31 39
30. N. Li, J. Lu, X. Xia, Q. Xu, and L. Wang Synthesis of third-order nonlinear optical polyacrylates containing an azobenzene side chain via atom transfer radical polymerization Dyes Pigments 80 2009 73 79
31. Z. Xin, F. Sanda, and T. Endo Synthesis and characterization of colored monomers based on 2-methylresorcinol Dyes Pigments 49 2001 1 7
32. S. Al-M Nayef Synthesis and characterization of new unsaturated polyesters and copolyesters containing azo groups in the main chain Eur Polym J 39 2003 1025 1033
33. V. Bojinov, and T. konstantinova Synthesis of polymerizable 1,8-naphthalimide dyes containing hindered amine fragment Dyes Pigments 54 2002 239 245
34. Z.H. Zhu, Q. Li, Q. Zeng, Li Zh, Li Zh, and J. Qin New azobenzene-containing polyurethanes: post-functional strategy and second-order nonlinear optical properties Dyes Pigments 78 2008 199 206
35. J. Luo, J. Qin, H. Kang, and C. Ye Synthesis and characterization of accordion main-chain azo-dye polymers for second-order optical non-linearity Polym Int 49 2000 1302 1307
36. X. Yu, C. Xinog, Y. You, L. Dong, and J. Yao Aromatic azo-polyamide electrolyte with liquid crystal structure and photoelectrical properties Synth Met 158 2008 375 378
37. K. Sieung Ju, K. Beom Jun, G. Dong Wook, K. Se Hun, P. Soo Young, and L. Ju Hyun Photoactive polyamideimides synthesized by the polycondensation of azo-dye diamines and rosin derivative J Appl Polym Sci 79 2001 687 695
38. E. Hamciuc, I. Sava, M. Bruma, T. Kopnick, B. Schulz, and B. Sapich New poly(amide-imide)s containing cinnamoyl and azobenzene group Polym Advan Technol 17 2006 641 646
39. Kh Faghihi, and M. Hagibeygi New polyamides containing azobenzene unites and hydantoin derivatives in ahain: synthesis and characterization J Eur Polym 39 2003 2307 2314
40. E. Gubbelmans, T. Verbiest, M. Van Beylen, A. Persoons, and C. Samyn Chromophore-functionalized polyamides with high-poling stabilities of the nonlinear optical effect at elevated temperature Polymer 43 2002 1581 1585
41. A.D. Becke Density functional thermochemistry. III. The role of exact exchange J Chem Phys 98 1993 5648 5652
42. A. Schaefer, H. Horn, and R. Ahlrichs Fully optimized contracted Gaussian basis sets for atoms Li to Kr J Chem Phys 97 1992 2571 2577
43. A. Schaefer, C. Huber, and R. Ahlrichs Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr J Chem Phys 100 1994 5829 5835
44. Granovsky AA. Firefly version 7.1.G, www http://classic.chem.msu.su/gran/ firefly/index.html.
45. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, and J.H. Jensen General atomic and molecular electronic structure system J Comput Chem 14 1993 1347 1363
46. J. Tomasi, B. Mennucci, and R. Cammi Quantum mechanical continuum salvation models Chem Rev 105 2005 2999 3094
47. G. Pavlovic, L. Racane, H. Cicak, and V.T. 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
48. 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
49. W.P. Oziminski, J.C. Dobrowolski, and A.P. Mazureka DFT studies on tautomerism of C5-substituted 1,2,4-triazoles J Mol Struct Theochem 680 2004 107 115
50. O. Yasuyo, H. Toshio, H. Mie, and M. Zenzo Substituent effects on the photofading of disperse azo dyes on poly(ethylene terephthalate) substrate Color Technol 126 2010 127 139
51. S. Tripathi, I. Vasudev, and A. Ray Photofading of azo dyes: a theoretical study Color Technol 124 2008 151 158
52. S.D. Kim, and E.J. Park Relation between chemical structure of yellow disperse dyes and their lightfastness Fiber Polym 2 2001 159 163
53. H. Willy, H. Klaus, G. Wilker, H. Obleier, and R. Winter Industrial organic pigment, production, properties application 3th ed. 2004 Wiley-VCH Weinheim
54. L. Wang, X. Pan, F. Wang, L. Yang, and L. Liu Structure-properties relationships investigation on the azo dyes derived from benzene sulfonamide intermediates Dyes Pigments 76 2008 636 645
55. P.F. Gordon, and P. Gregory Organic chemistry in colour 1983 Springer-Verlag Berlin p. 96-108
56. J. Bandekar, and G. Zundel The role of CO transition dipole-dipole coupling interaction in uracil Spectrochim Acta 39A 1983 337 341