SYNTHESIS, CHARACTERIZATION AND SPECTROSCOPIC STUDIES ON TAUTOMERISM AND ACIDITY CONSTANTS OF CERTAIN 4- (PHENYLDIAZENYL) BENZENE-1,3-DIOL DERIVATIVES
Öz
In this study, monoazo dyes were synthesized through the diazotization of several substituted aminobenzenes and couplings with benzene-1,3-diols. The chemical structures of these compounds were characterized using spectroscopic techniques. The tautomeric properties of the 4-(phenyldiazenyl)benzene-1,3-diol derivative compounds were examined using UV-Vis. spectrophotometry in pure polar or apolar media (dimethyl sulfoxide, ethanol, chloroform, benzene and cyclohexane) under acidic and basic conditions at 25 ± 1 °C, 35 ± 1 °C and 45 ± 1 °C. The percentage of the azo-hydrazone tautomers was calculated for all of the compounds. The UV-Vis. analysis reveals that the azo form is dominant in the presence of azo-hydrazone tautomerism for all azo dyes. Concurrently, the acidity constants for these derivatives were determined using a UV-Vis. spectroscopic technique at 25 °C (± 0.1 °C).
Anahtar Kelimeler
Azo dyes, Azo-hydrazone tautomerism, Ionization constants, Acidity constants
Kaynakça
- Silva, C. G., Wang, W. & Faria, J. L. Photocatalytic and Photochemical Degradation of Mono-, Di- and Tri-azo Dyes in Aqueous Solution Under UV Irradiation. Journal of Photochemistry and Photobiology A: Chemistry, 181, 314-324, 2006.
- Isak, S. J., Eyring, E. M., Spikes, J. D. & Meekins, P. A. Direct Blue Dye Solutions: Photo Properties. Journal of Photochemistry and Photobiology A: Chemistry, 134, 77-85, 2000.
- Joshi, H., Kamounah, F. S., Gooijer, C., van der Zwan, G. & Antonov, L. Excited State Intramolecular Proton Transfer in Some Tautomeric Azo Dyes and Schiff Bases Containing an Intramolecular Hydrogen Bond. Journal of Photochemistry and Photobiology A: Chemistry. 152, 183-191, 2002.
- Bauer, C., Jacques, P. & Kalt, A. Photooxidation of an Azo Dye Induced by Visible Light Incident on the Surface of Tio2. Journal of Photochemistry and Photobiology A: Chemistry. 140, 87-92, 2001.
- Wang, J. & Ha, C. A Colorimetric and Fluorescent Turn-On Chemosensor for Zn2+ Based on an Azobenzene-Containing Compound. Tetrahedron, 65, 6959–6964, 2009.
- Wang, Y., Han, P., Xu, H., Wang, Z., Zhang, X. & Kabanov, A. V. Photocontrolled Self-Assembly and Disassembly of Block Ionomer Complex Vesicles: A Facile Approach Toward Supramolecular Polymer Nanocontainers. Langmuir, 26, 709-715, 2010.
- Lee, H. Y., Song, X., Park, H., Baik M. & Lee D. Torsionally Responsive C3-Symmetric Azo Dyes: Azo−Hydrazone Tautomerism, Conformational Switching, and Application for Chemical Sensing. Journal of the American Chemical Society, 132, 12133–12144, 2010.
- Inoue, Y., Kuad, P., Okumura, Y., Takashima, Y., Yamaguchi, H. & Harada, A. Thermal and Photochemical Switching of Conformation of Poly(ethylene glycol)-Substituted Cyclodextrin with an Azobenzene Group at the Chain End. Journal of the American Chemical Society, 129, 6396–6397, 2007. [9] Yager, K. G. & Barrett, J. C. Novel Photo-Switching Using Azobenzene Functional Materials. Journal of Photochemistry and Photobiology A: Chemistry, 182, 250–261, 2006.
- Ding, L. & Russell, T. P. A Photoactive Polymer with Azobenzene Chromophore in The Side Chains. Macromolecules, 40, 2267–2270, 2007.
- Gao, J., He, Y., Xu, H., Song, B., Zhang, X., Wang, Z. & Wang, X. Azobenzene-Containing Supramolecular Polymer Films for Laser-Induced Surface Relief Gratings. Chemistry of Materials, 19, 14–17, 2007.