Benzothiazole-Based Bis-azo Cationic Fluorescent Dyes with Extended Conjugated Systems: Synthesis and Properties

Authors

  • Frahnaz Nourmohammadian Center of Excellence for Color Science and Technology
  • Mohammad Yousef Alikhani Hamadan University of Medical Sciences
  • Mahnaz Davoudzadeh Gholami Center of Excellence for Color Science and Technology
  • Ali Ashtiani Abdi Center of Excellence for Color Science and Technology

DOI:

https://doi.org/10.6000/1929-5030.2015.04.02.1

Keywords:

Benzothiazole, Azo Dyes, Fluorescence, Cationic dye, Antibacterial, Solvatochromism

Abstract

Sixteen novel 2-aminobenzothiazole based dichromophoric cationic azo dyes were synthesized and their photophysical properties studied. The colors of the synthesized azo dyes were violet to blue with high molecular extinction coefficient ranged between 2.6 - 4.7— 104 (M-1.cm-1). All of the dyes showed unique fluorescence emission at a broad range of 409–494 nm. The absorption and emission spectral changes of selected dyes were also analyzed in solvents with different polarity. Furthermore, the antibacterial activities of the dyes were evaluated against gram positive and negative bacteria including S. aureus, S. epidermidis, E. coli, and P. aeruginosa and different concentrations of dyes showed an anti-gram positive bacterial activity.

Author Biography

Mohammad Yousef Alikhani, Hamadan University of Medical Sciences

Department of Microbiology, Faculty of Medicine

References


[1] Zhang M, Lu W-T, Ruan W, Zhang H-J, Wen T-B. Coppercatalyzed solvent-free redox condensation of benzothiazoles with aldehydes or benzylic alcohols. Tetrahedron Lett 2014; 55: 1806-9. http://dx.doi.org/10.1016/j.tetlet.2014.01.120
[2] Tong Y, Pan Q, Jiang Z, Miao D, Shi X, Han S. A simple approach to benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine under solvent-free and catalyst-free conditions. Tetrahedron Lett 2014; 55: 5499- 503. http://dx.doi.org/10.1016/j.tetlet.2014.08.037
[3] Prajapati NP, Vekariya RH, Borad MA, Patel HD. Recent advances in the synthesis of 2-substituted benzothiazoles: a review. Rsc Advances 2014; 4: 60176-208. http://dx.doi.org/10.1039/C4RA07437H
[4] Pan L, Yu L, Wu Z, Li Z, Xiang H, Zhou X. Quaternary ammonium salt as alkylation agent in three-component reactions for the synthesis of benzothiazoles in water. Rsc Advances 2014; 4: 27775-9. http://dx.doi.org/10.1039/c4ra04145c
[5] Naeimi H, Tarazian R. Efficient and Facile Catalyst-free OnePot Synthesis and Characterization of Some Novel Bis(2- benzothiazole) Derivatives. J Heterocycl Chem 2014; 51: 566-71. http://dx.doi.org/10.1002/jhet.1956
[6] Kheder NA, Mabkhot YN, Zahian FR, Mohamed SS. Regioselective Synthesis of Some Pyrazole Scaffolds Attached to Benzothiazole and Benzimidazole Moieties. J CHEMISTRY 2014.
[7] Mohamed KS, Abdulaziz NM, Fadda AA. Synthesis of Some New Pyridine and Pyrimidine Derivatives Containing Benzothiazole Moiety. J Heterocycl Chem 2013; 50: 645-9. http://dx.doi.org/10.1002/jhet.1672
[8] Shindy HA, El-Maghraby MA, Eissa FM. Synthesis and colour spectrophotometric measurements of some novel merocyanine dyes. Dyes Pigm 2012; 92: 929-35. http://dx.doi.org/10.1016/j.dyepig.2011.03.019
[9] Shi Q-Q, Sun R, Ge J-F, Xu Q-F, Li N-J, Lu J-M. A comparative study of symmetrical and unsymmetrical trimethine cyanine dyes bearing benzoxazolyl and benzothiazolyl groups. Dyes Pigm 2012; 93: 1506-11. http://dx.doi.org/10.1016/j.dyepig.2011.11.001
[10] Deligeorgiev T, Kaloyanova S, Vasilev A. A novel general method for preparation of neutral monomethine cyanine dyes. Dyes Pigm 2011; 90: 170-6. http://dx.doi.org/10.1016/j.dyepig.2010.10.012
[11] Zajac M, Hrobarik P, Magdolen P, Foltinova P, Zahradnik P. Donor-pi-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity. Tetrahedron 2008; 64: 10605-18. http://dx.doi.org/10.1016/j.tet.2008.08.064
[12] Avagyan R, Luongo G, Thorsen G, Ostman C. Benzothiazole, benzotriazole, and their derivates in clothing textiles-a potential source of environmental pollutants and human exposure. Environ Sci Pollut Res Int 2014.
[13] Kharbanda C, Alam MS, Hamid H, Javed K, Bano S, Dhulap A, et al. Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents. Biorg Med Chem 2014; 22: 5804-12. http://dx.doi.org/10.1016/j.bmc.2014.09.028
[14] Yang Y, Li B, Zhang LM. Design and synthesis of triphenylamine-malonitrile derivatives as solvatochromic fluorescent dyes. Sensors Actuators B: Chem 2013; 183: 46- 51. http://dx.doi.org/10.1016/j.snb.2013.03.108
[15] Rufchahi EOM, Yousefi H, Mohammadinia M. Synthesis and spectral properties of some azo disperse dyes containing a benzothiazole moiety. J Mol Liq 2013; 188: 173-7. http://dx.doi.org/10.1016/j.molliq.2013.08.021
[16] Popova A, Christov M, Vasilev A, Zwetanova A. Mono- and dicationic benzothiazolic quaternary ammonium bromides as mild steel corrosion inhibitors. Part I: Gravimetric and voltammetric results. Corros Sci 2011; 53: 679-86. http://dx.doi.org/10.1016/j.corsci.2010.10.005
[17] Popova A, Christov M, Vasilev A. Mono- and dicationic benzothiazolic quaternary ammonium bromides as mild steel corrosion inhibitors. Part II: Electrochemical impedance and polarisation resistance results. Corros Sci 2011; 53: 1770-7. http://dx.doi.org/10.1016/j.corsci.2011.01.055
[18] Naik S, Alves CMA, Coutinho PJG, Goncalves MST. N- (Di)icosyl-Substituted Benzo a phenoxazinium Chlorides: Synthesis and Evaluation as Near-Infrared Membrane Probes. European J Org Chem 2011: 2491-7. http://dx.doi.org/10.1002/ejoc.201001579
[19] Fujii K, Kuroda T, Sakoda K, Iyi N. Fluorescence resonance energy transfer and arrangements of fluorophores in integrated coumarin/cyanine systems within solid-state twodimensional nanospace. J Photochem Photobiol A 2011; 225: 125-34. http://dx.doi.org/10.1016/j.jphotochem.2011.10.009
[20] Pandey AK, Deakin PC, Jansen-Van Vuuren RD, Burn PL, Samuel IDW. Photo-Rechargeable Battery Effect in First Generation Cationic-Cyanine Dendrimers. Adv Mater 2010; 22: 3954-+. http://dx.doi.org/10.1002/adma.200904464
[21] Jedrzejewska B, Pietrzak M, Paczkowski J. Tetramethylammonium phenyltrialkylborates as co-initiators with novel two-cationic styrylbenzimidazolium dyes in highly efficient, visible light polymerization of acrylate. J Photochem Photobiol A 2010; 214: 276-83. http://dx.doi.org/10.1016/j.jphotochem.2010.07.012
[22] Kim JY, Kim TH, Kim DY, Park N-G, Ahn K-D. Novel thixotropic gel electrolytes based on dicationic bisimidazolium salts for quasi-solid-state dye-sensitized solar cells. J Power Sources 2008; 175: 692-7. http://dx.doi.org/10.1016/j.jpowsour.2007.08.085
[23] Suzuki T, Iwai T, Ohta E, Kawai H, Fujiwara K. Electrochiroptical systems based on biphenyl-2,2 '-diyl-type dicationic dyes: strong chiroptical signals through the transmission of point chirality to axial chirality. Tetrahedron Lett 2007; 48: 3599-603. http://dx.doi.org/10.1016/j.tetlet.2007.03.080
[24] Suzuki T, Iwashita S, Yoshino T, Kawai H, Fujiwara K, Ohkita M, et al. The first stable tetraarylacenaphthenequinodimethanes exhibiting electrochromism with 'writeprotect' option: preparation, highly deformed structure, and reversible interconversion with acenaphthylene-5,6-diyl dicationic dyes. Tetrahedron Lett 2006; 47: 467-71. http://dx.doi.org/10.1016/j.tetlet.2005.11.059
[25] Yin G-L, Li Y, Tang K, Jin X-F, Chen X-G, Li L, et al. Synthesis and biological evaluation of 2-(3- butynoicamidophenyl) benzothiazole derivatives as antitumor agents. Yao xue xue bao = Acta pharmaceutica Sinica 2014; 49: 888-95.
[26] Wang S, Chen Y, Zhao S, Xu X, Liu X, Liu B-F, et al. Synthesis and biological evaluation of a series of benzoxazole/benzothiazole-containing 2,3-dihydrobenzo b 1,4 dioxine derivatives as potential antidepressants. Bioorg Med Chem Lett 2014; 24: 1766-70. http://dx.doi.org/10.1016/j.bmcl.2014.02.031
[27] Singh M, Singh SK. Benzothiazoles: How Relevant in Cancer Drug Design Strategy? Anticancer Agents Med Chem 2014; 14: 127-46. http://dx.doi.org/10.2174/18715206113139990312
[28] Singh M, Gangwar M, Nath G, Singh SK. Synthesis, DNA cleavage and antimicrobial activity of 4-thiazolidinonesbenzothiazole conjugates. Indian J Exp Biol 2014; 52: 1062- 70.
[29] Riswan Ahamed MA, Azarudeen RS, Kani NM. Antimicrobial applications of transition metal complexes of benzothiazole based terpolymer: synthesis, characterization, and effect on bacterial and fungal strains. Bioinorg Chem Appl 2014; 2014: 764085-. http://dx.doi.org/10.1155/2014/764085
[30] Ma J, Zhang G, Han X, Bao G, Wang L, Zhai X, et al. Synthesis and Biological Evaluation of Benzothiazole Derivatives Bearing the ortho-Hydroxy-N-acylhydrazone Moiety as Potent Antitumor Agents. Arch Pharm 2014; 347: 936-49. http://dx.doi.org/10.1002/ardp.201400230
[31] Li H, Wang X-M, Wang J, Shao T, Li Y-P, Mei Q-B, et al. Combination of 2-methoxy-3-phenylsulfonylaminobenzamide and 2-aminobenzothiazole to discover novel anticancer agents. Biorg Med Chem 2014; 22: 3739-48. http://dx.doi.org/10.1016/j.bmc.2014.04.064
[32] Kumbhare RM, Dadmal TL, Pamanji R, Kosurkar UB, Velatooru LR, Appalanaidu K, et al. Synthesis of novel fluoro 1,2,3-triazole tagged amino bis(benzothiazole) derivatives, their antimicrobial and anticancer activity. Med Chem Res 2014; 23: 4404-13. http://dx.doi.org/10.1007/s00044-014-1006-0
[33] Wang C, Xu F, Niu Y, Wu Y, Sun J, Peng Y, et al. Synthesis and Biological Evaluations of 3-Benzothiazol-2-yl Coumarin Derivatives as MEK1 Inhibitors. Lett Drug Des Discov 2013; 10: 727-32. http://dx.doi.org/10.2174/15701808113109990012
[34] Patel AB, Sahoo SK, Chikhalia KH, Kumari P. Design, Synthesis and Computational Studies of New Benzothiazole Substituted Quinazolines as Potential Antimicrobial Agents. Lett Drug Des Discov 2013; 10: 957-66. http://dx.doi.org/10.2174/15701808113109990025
[35] Kamal A, Faazil S, Ramaiah MJ, Ashraf M, Balakrishna M, Pushpavalli SNCVL, et al. Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells. Bioorg Med Chem Lett 2013; 23: 5733-9. http://dx.doi.org/10.1016/j.bmcl.2013.07.068
[36] Liu ZR, Rill RL. N,N'-bis 3,3'-(dimethylamino)propylamine - 3,4,9,10-perylenetetracarboxyl ic diimide, a dicationic perylene dye for rapid precipitation and quantitation of trace amounts of DNA. Anal Biochem 1996; 236: 139-45. http://dx.doi.org/10.1006/abio.1996.0142
[37] Nourmohammadian F, Gholami MD. Synthesis and Characterization of Some Novel Dichromophoric Cyanine Dyes. Synth Commun 2009; 39: 1981-91. http://dx.doi.org/10.1080/00397910802630195
[38] Nourmohammadian F, Gholami MD. Two Novel Push-Pull Series of Benzothiazole-Based Dyes: Synthesis and Characterization. Helv Chim Acta 2012; 95: 1548-55. http://dx.doi.org/10.1002/hlca.201200080
[39] Nourmohammadian F, Gholami MD. Synthesis of Fluorescent Dichromophoric Benzothiazole-Based Polyenes. Lett Org Chem 2012; 9: 720-31. http://dx.doi.org/10.2174/157017812803901863
[40] Reichardt C. Solvatochromic dyes as empirical indicators of solvent polarity. Chimia 1991; 45: 322-4.
[41] Reichardt C. Solvatochromic dyes as solvent polarity indicators. Chem Rev 1994; 94: 2319-58. http://dx.doi.org/10.1021/cr00032a005
[42] Suman GR, Bubbly SG, Gudennavar SB, Thipperudrappa J, Roopashree B, Gayathri V, et al. Effect of solvents on photophysical properties and quenching of 2-{
[3-(1Hbenzimidazole-2-yl) phenyl] carbonoimidoyl}phenol. Luminescence 2014. http://dx.doi.org/10.1002/bio.2794
[43] Pannipara M, Asiri AM, Alamry KA, Arshad MN, El-Daly SA. Spectroscopic investigation, effect of solvent polarity and fluorescence quenching of a new D-pi-A type chalcone derivative. J Fluoresc 2014; 24: 1629-38. http://dx.doi.org/10.1007/s10895-014-1449-1
[44] Ceron-Carrasco JP, Jacquemin D, Laurence C, Planchat A, Reichardt C, Sraidi K. Solvent polarity scales: determination of new E-T(30) values for 84 organic solvents. J Phys Org Chem 2014; 27: 512-8. http://dx.doi.org/10.1002/poc.3293
[45] Martinez-Martinez V, Lim J, Banuelos J, Lopez-Arbeloa I, Miljanic OS. Strong intramolecular charge transfer emission in benzobisoxazole cruciforms: solvatochromic dyes as polarity indicators. PCCP 2013; 15: 18023-9. http://dx.doi.org/10.1039/c3cp53527d
[46] Gilani SJ, Khan SA. Synthesis and pharmacological evaluation of N-(6-chlorobenzo d thiazol-2-yl)hydrazine carboxamide derivatives of benzothiazole. Med Chem Res 2013; 22: 3316-28. http://dx.doi.org/10.1007/s00044-012-0329-y Received on 20-02-2015 Accepted on 13-05-2015 Published on

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Published

2015-06-16

How to Cite

Nourmohammadian, F., Alikhani, M. Y., Gholami, M. D., & Abdi, A. A. (2015). Benzothiazole-Based Bis-azo Cationic Fluorescent Dyes with Extended Conjugated Systems: Synthesis and Properties. Journal of Applied Solution Chemistry and Modeling, 4(2), 83–94. https://doi.org/10.6000/1929-5030.2015.04.02.1

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