Novel Aza-Substituted Benzothiazol and 1,2,4-Triazol Cyanine Dyes: Synthesis, Characterization and Properties


Journal: Vol.6, No.1, Winter 2013 - Article 5   Pages :   Until 



Article Code:
PCCC-29-09-2012-212

Authors:
Farahnaz Nourmohammadian: Institute of Color Science and Technology - Department of Organic Colorants


Article's abstract:

Series of novel dichromophoric cyanine dyes based on 2-aminobenzothiazoles and 3-amino-1,2,4 -triazole have been synthesized in high yields. All the dyes have been classified as disperse dyes. Besides their electronic spectroscopic properties, high dye-uptakes on polyester, excellent fastness properties, highly extinction coefficients, and broad solvatochromic effects have been observed in these novels disperse dyes. The derivatives of amino triazole were appropriate as pH indicator in the range of 11-13.


Keywords:
Dichromophoric, cyanine dyes, solvatochromic effects, aminobenzothiazole.

References:
1. H. Faustino, R. M. El-Shishtawy, L. V. Reis, P. F. Santos, P. Almeida, 2- Nitrosobenzothiazoles: useful synthons for new azobenzothiazole dyes, Tetrahedron Lett, 49(2008), 6907-6909.#2. H. Faustino, C. R. Brannigan, L. V. Reis, P. F. Santos, P. Almeida, Novel azobenzothiazole dyes from 2-nitrosobenzothiazoles, Dyes Pigm., 83(2009), 88-94.#3. S. Frere, V. Thiery, C. Bailly, Besson, T. Novel 6-substituted benzothiazol-2-yl indolo[1,2-c] quinazolines and benzimidazo[1,2-c]quinazolines. Tetrahedron, 59(2003), 773-779.#4. M. R. Mazieres, C. Duprat, J. G. Wolf, A. D. Roshal, pH dependent spectral properties and electronic structure of benzothiazole containing cyanine dyes, Dyes Pigm., 80(2009), 355-360.#5. J. Soko1owska, R. 1. Podsiad1y, E. Sochocka, Synthesis and properties of some disazo disperse dyes derivatives of 2-amino-6-phenylazobenzothiazole and 2-amino-6-(4#-nitro)-Phenylazobenzothiazole, Dyes Pigm., 72(2007), 223-227.#6. L. Racane, V.Tralic-Kulenovic, D.W.Boykin, G. Karminski-Zamola, Synthesis of new cyano-substituted bis-benzothiazolyl arylfurans and arylthiophenes. Molecules 8 (2003), 342-348.#7. M. Zajac, P. Hrobarik, P. Magdolen, P. Foltinova, P. Zahradnik, Donor-pi-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity, Tetrahedron, 64(2008), 10605-10618.#8. L. Shuttleworth, M. A. Weaver, In: D. R. Waring, G. Hallas,The chemistry and application of dyes. New York, Plenum, 1990 [chapter IV].#9. K. Gharanjig, F. Ameri, F. S. Dadras, A. Khosravi, Novel naphthalimide based azo disperse dyes for dyeing of polyester fabrics, Prog. Color Colorats Coats., 4(2011), 27-37.#10. N. O. Mahmoodi, N. Naseri, E. Asadollahi, B. Ghalami-Choobar, R. H. Sajedi, Design and synthesis of new symmetrical schiff bases, Prog. Color Colorats Coats., 4(2011), 113-120.#11. M. E. Olya, H. Aleboyeh, A. Aleboyeh, Decomposition of a dye in aqueous solutions by KMNO4/UV/H2O2 process, Prog. Color Colorats Coats., 5(2012), 41-46.#12. A. Mohammadi, M. R. Yazdanbakhsh, N. Mahmoodi, Synthesis and charachterization of some novel linear azo-azomethine compounds based on 1-bromo-4-[4-(4-nitrophenylazo)phenoxy] butane, Prog. Color Colorats Coats., 5(2012), 23-33.#13. F. Nourmohammadian, M. D. Gholami, An investigation of dyeability of Acrylic fiber via microwave irradiation, Prog. Color Colorats Coats., 1(2008), 57-63.#14. J. Belmar, M. Parra, C. Zuniga, C. Perez, C. Munoz, New liquid crystals containing the benzothiazol unit: amides and azo compounds, Liq. Cryst., 26(1999), 389-396.#15. M. C. Davis, A. P. Chafin, R. A. Hollins, L. C. Baldwin, E. D. Erickson, P. Zarras, E. C. Drury, Synthesis of an isophorone-based nonlinear optical chromophore, Synth. Commun, 34(2004), 3419-3429.#16. A. C. Razus, L. Birzan, N. M.Surugiu, A. C. Corbu, F. Chiraleu, Syntheses of azulen-1-yl-benzothiazol-2-yl diazenes, Dyes Pigm., 2007(74), 26-33.#17. M. C. Davis, R. A, Hollins, B. Douglas, Synthesis of a thiophene-based nonlinear optical chromophore, Synth. Commun, 36(2006), 3515-3523. #18. E. Font-Sanchis, F. J. Cespedes-Guirao, A. Sastre-Santos, B. Villacampa, J. Orduna, R. Alicante, F. Fernandez-Lazaro, Synthesis and nonlinear optical properties of chromophores for photorefractive polymer materials, Tetrahedron, 65(2009), 4513-4520.#19. M. A. Salvador, L. V. Reis, P. Almeida, P. F. Santos, Delocalized cationic azo dyes containing a thiazole moiety, Tetrahedron, 64(2008), 299-303.#20. Y. H. Ebeada, M. A. Selima, S. A. Ibrahimb, Solvatochromic, acid–base features and time effect of some azo dyes derived from 1,3-benzothiazol-2-ylacetonitrile: Experimental and semiempirical investigations, Spectrochim. Acta, Part A, 75(2010), 760-768.#21. A. Emandi, I. Serban, R. Bandula, Synthesis of some new solvatochromic 1(4)-substituted Pyrazol-5-one Azo derivatives, Dyes Pigm., 41(1999), 63-77.#22. N. M. Rageh, Electronic spectra, solvatochromic behavior and acid-base properties of some azo cinnoline compounds, Spectrochim. Acta A, 60(2004), 103-109.#23. E. Buncel, S. Rajagopal, Solvatochromic studies of novel azo merocyanine dyes. The π*azo scale of solvent polarity, J. Org. Chem., 54(1989), 798-809.#24. F. Nourmohammadian, M. Davoudzadeh Gholami, Synthesis and characterization of some novel dichromophoric cyanine dyes, Synth. Commun., 39( 2009), 1981-1991.#25. F. Nourmohammadian, M. Davoudzadeh Gholami, Synthesis of fluorescent dichromophoric benzothiazole-based polyenes, Lett. Org. Chem., 9(2012), 720-731.#26. F. Nourmohammadian, M. Davoudzadeh Gholami, Two Novel Push-Pulls Series Of Benzothiazole-Based Dyes: Synthesis And Characterization, Helv. Chim. Acta, 95(2012), 1548-1555.#27. E. Ross, J. KO, R. Naumann, W. Fischer, W. D. Mayer, G. Wieland, Indicator reagents, Ullmann’s encyclopedia of industrial chemistry, 6th ed., Vol. 17, Weinheim: VCH, 2003, 645-656.#28. K. Hunger, Industrial dyes: chemistry, properties and applications, Wiely-VCH Publishing Company, 2002, 526-537.#29. F. Nourmohammadian, M. Davoodzadeh, A. A. Alizadeh, New cyclopentadiene derivatives as novel pH indicators, Dyes Pigm., 74(2007), 741-743.#30. G. J. H. M. Wilfried, W. J. VanSark, K. Barnham, L. H. Slooff, A. J. Chatten, A. Büchtemann, A. Meyer, S. J. McCormack, R. Koole, D. J. Farrell, R. Bose, E. E. Bende, A. R. Burgers, T. Budel, J. Quilitz, M. Kennedy, T. Meyer, C. D. M. Donegá, A. Meijerink, D. Vanmaekelbergh, Luminescent Solar Concentrators - A review of recent results, Optics Express, 16(2008), 21773-21791.


Article's file
Page view: 2934
Article's download quantity : 632


Article System Login
Introduction

Manager-in-Chief:
Prof. Zahra Ranjbar
Editor-in-Chief:
Dr. Farahnaz Nourmohammadian
Assistant Editor:
Dr. Mozhgan Hosseinnezhad
ISSN:
2008-2134
ISSN (online):
2383-1790
Publisher:
Institute for Color Science and Technology (ICST)

Quick Access
Publications
E-Vote
What is your opinion about the manuscript subscription system of PCCC website?
Excellent
Good
Fair
Poor
Website Statistics
Page view:2,935
Online Visitors:37