Synthesis, structural characterization and thermal studies of a novel reagent 1-[(5-benzyl-1,…
7
8
9
. Ahlstr o¨ m L, Eskilsson CS, Bj o¨ rklund E. Determination of
banned azo dyes in consumer goods. Trends Anal Chem.
005;24:49–56.
. Pytlakowska K, Kozik V, Dabioch M. Complex-forming organic
ligands in cloud-point extraction of metal ions: a review. Talanta.
Conclusions
2
In conclusion, we have synthesized and characterized a
new azo reagent 1-[(5-benzyl-1,3-thiazol-2-yl)diazenyl]-
naphthalene-2-ol. It was prepared in the efficient synthetic
procedure involving Meerwein arylation, diazotization and
diazocoupling. This method can be an excellent synthetic
route to new diazo colors as potential analytical reagents.
The obtained compound is thermally stable up to
2
013;100:202–28.
. Wang H, Zhang HS, Cheng JK. Studies on 2-(2-thiazolylazo)-5-
diethylaminophenol as a precolumn derivatizing reagent in the
separation of platinum group metals by high performance liquid
chromatography. Talanta. 1999;48:1–7.
0. Lee W, Lee S-E, Lee C-H, Kim Y-S, Lee Y-I. A chelating resin
containing 1-(2-thiazolylazo)-2-naphthol as the functional group;
synthesis and sorption behavior for trace metal ions. Microchem
J. 2001;70:195–203.
1
1
71 °C. The further decomposition of the substance takes
place in five consecutive stages and ends at *680 °C.
Thiazolylazonaphthol dye was found to be a sensitive and
selective analytical reagent for the determination of such
11. Baliza PX, Ferreira SLC, Teixeira LSG. Application of pyridy-
lazo and thiazolylazo reagents in flow injection preconcentration
systems for determination of metals. Talanta. 2009;79:2–9.
2
?
2?
2?
transition metal ions as Cd , Hg , Pd . Moreover,
according to the results of the ionization constants deter-
mination, the substance 5 could be successfully used as the
indicator in acid–base titrations. Furthermore, the reviewed
azo dye may be active against cancer cells because of the
presence of thiazol heterocycle.
1
2. Yamaki RT, Vieira DR, Novaes CG, de Oliveira HR, Lemos VA.
Application of a thiazolylazo dye as an acid-base indicator and
determination of its acid ionization constants. Quim Nova.
2
009;32:1943–6.
1
3. Bezerra MA, Arruda MAZ, Ferreira SLC. Cloud point extraction
as a procedure of separation and preconcentration for metal
determination using spectroanalytical techniques: a review. Appl
Spectrosc Rev. 2005;40:269–99.
Acknowledgements The authors are grateful to the Government of
the Republic of Poland for their financial support of this work
according to the program ‘‘Polish Erasmus for Ukraine’’ for graduate
students. We also thank Prof Tomasz Ruman from the Department of
Polymer Technology, Rzeszow University of Technology, for
recording NMR spectra, and Dr Beata Mossety-Leszczak from the
Department of Industrial and Materials Chemistry for carrying out
DCS studies.
14. Fan X, Zhang G, Zhu C. Synthesis of 2-[2-(5-methylbenzothia-
zolyl) azo]-5-dimethylaminobenzoic acid and its application to
the spectrophotometric determination of nickel. Analyst.
1998;123:109–12.
15. Bhalotra A, Puri BK. Column preconcentration and second
derivative spectrophotometric trace determination of scandium in
standard biological and synthetic samples using 1-(2-Thiazoly-
lazo)-2-naphthol. Anal Sci. 2000;16:507–11.
1
6. Eshwar MC, Sharma CD. Rapid spectrophotometric determina-
0
Open Access This article is distributed under the terms of the
distribution, and reproduction in any medium, provided you give
appropriate credit to the original author(s) and the source, provide a
link to the Creative Commons license, and indicate if changes were
made.
tion of vanadium(V) with 1-(2 -thiazolylazo)-2-naphthol.
Microchem J. 1987;35:27–9.
17. Rathaiah GV, Eshwar MC. Rapid spectrophotometric determi-
nation of chromium(III) with 1-(2-Thiazolylazo)-2-naphthol in
presence of surfactant. Bull Chem Soc Jpn. 1985;58:2447–8.
18. Wang L-L, Wang J-Q, Zheng Z-X, Xiao P. Cloud point extraction
combined with high-performance liquid chromatography for
speciation of chromium(III) and chromium(VI) in environmental
sediment samples. J Hazard Mater. 2010;177:114–8.
1
9. Chavan SS, Sawant VA. Synthesis, structural characterization,
thermal and electrochemical studies of Mn(II), Co(II), Ni(II) and
Cu(II) complexes containing thiazolylazo ligands. J Mol Struct.
2010;965:1–6.
References
1
. Furukawa M. Syntheses and spectrophotometric studies of 2-(2-
thiazolylazo)- and 2-(2-benzothiazolylazo)-5-dimethylaminoben-
zoic acids as analytical reagents: determination of nickel. Anal
Chim Acta. 1982;140:281–9.
20. Ferreira SLC, Nano RMW. Use of 1-(2-thiazolylazo) 2-naphthol
in rapid determination of iron in geological matrices. Talanta.
1994;41:1937–41.
2
3
4
5
. Devia A, de Sosa GZ, Estrada M, Nemzoff G. Theoretical studies
on the molecular structure of 1,3-benzenediamine,4-(2-thiazoly-
lazo). J Mol Struct Theochem. 1989;188:141–7.
. Lemos VA, Santos ES, Santos MS, Yamaki RT. Thiazolylazo
dyes and their application in analytical methods. Microchim
Acta. 2007;158:189–204.
. Wang S, Shen S, Xu H, Gu D, Yin J, Dong X. Metallized thia-
zolylazo dyes as optical recording materials. Mater Sci Eng
B-Solid. 2001;79:45–8.
. Hyeyoung P, Eung-Ryul K, Dong JK, Haiwon L. Synthesis of
metal-azo dyes and their optical and thermal properties as
recording materials for DVD-R. Bull Chem Soc Jpn.
21. Niazi A, Yazdanipour A. Simultaneous spectrophotometric
determination of cobalt, copper and nickel using 1-(2-thiazoly-
lazo)-2-naphthol by chemometrics methods. Chinese Chem Lett.
2008;19:860–4.
22. Jamali MR, Madadjo A, Rahnama R. Determination of nickel
using cold-induced aggregation microextraction based on ionic
liquid followed by flame atomic absorption spectrometry. J Anal
Chem. 2014;69:426–31.
3 4
23. Samadi A, Amjadi M. Magnetic Fe O @C nanoparticles modi-
fied with 1-(2-thiazolylazo)-2-naphthol as a novel solid-phase
extraction sorbent for preconcentration of copper (II). Microchim
Acta. 2015;182:257–64.
2
002;75:2067–70.
24. Ferreira SLC, Araujo NML, Santos AB, Dantas AF. Spinola
Costa AC. Spectrophotometric determination of zinc in copper-
base alloys with TAN. Microchim Acta. 1995;118:123–9.
6
. Ogawa K. Two-photon absorbing molecules as potential materi-
als for 3D optical memory. Appl Sci. 2014;4:1–18.
123