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An experimental study on relationship between hammett substituent constant and electronic absorption wavelength of some azo dyes

Year 2011, , 7 - 11, 23.12.2011
https://doi.org/10.17678/beuscitech.47153

Abstract

In this study, absorption spectra of sixteen azo dyes have been recorded in various solvents. These azo dyes have substituents such as OH, SO3H, Cl, I, NO2, C2H5 and OCH3 in different positions of phenyl ring. There is a shift in ?max whose amount is dependent upon the type and position of substituent on the ring. The effects of substituent on the absorption spectra of azo dyes are interpreted by correlation of absorption maximum wavelengths (nm) with the hammett substituent parameters. Charge transfer transitions are observed in inverse direction for azo dyes with electron acceptor substituent compared to azo dyes with electron donor

References

  • Aksu N (2007). Synthesis of monoazo compounds of some substitue anilin with benzene-1,3-diol and investigation of their tautomeric equilibrium, Msc Thesis, Anadolu University, Eskişehir, Turkey.
  • Bartkiewicz S, Matczyszyn K, Miniewicz A, Kajzar F (2001). High gain of light in photoconducting polymer– nematic liquid crystal hybrid structures. Opt Commun 187, 257-261.
  • Ermis E (2003). Bazı 2-substitue anilin ve benzen-1,3- diol ile monoazo bileşiklerinin sentezlenmesi. Master Thesis, Anadolu University, Fen Bilimleri Enstitusu, Eskişehir, Turkey.
  • Gibson WM, Shannon PJ, Shao-Tang S, Swetlin BJ (1991). Surface-mediated alignment of nematic liquid crystals with polarized laser light. Nature 351, 49-50.
  • Giménez R, Millaruelo H, Piňol M, Serrano JL, Viňuales A, Rosenhauer R, Fischer T, Stumpe J (2005). Synthesis, thermal and optical properties of liquid crystalline terpolymers containing azobenzene and dye moieties. Polymer 46, 9230-9242.
  • Gregory P (1991). High-technology applications of organic colorants plenum, New York.
  • Gülseven Y, Taşal E, Sıdır İ, Güngor T, Berber H, Öğretir C (2009). Solvatochromic effect studies on the absorption spectra of 4-(2-ethylphenyl) diazenyl) benzene-1,3-diol and 2-((2-ethylphenyl) diazenyl) benzene-1,3,5-triol molecules. Int J Hydrogen Energ 34, 5255-5259.
  • Gülseven Sıdır Y, Sıdır İ, Berber H, Taşal E (2011a). UV- spectral changes for some azo compounds in the presence of different solvents. J Mol Liq 162, 148–154.
  • Gülseven Sıdır Y, Sıdır İ, Taşal E, Ermiş E (2011b). Studies on the electronic absorption spectra of some monoazo derivatives. Spectrochim Acta Part A: Molec and Biomol Spectros 78, 640-647.
  • Hansch C, Leo A, Taft RW (1991). A Survey of Hammett Substituent Constants and Resonance and Field Parameters. Chem Rev 91, 165-195.
  • Issa RM, Assar SS, Dessouki HM (1992). Halochromic and electronic absorption spectral properties for some azo- azomethine dyes. Egyptian J Chem 35, 321-334.
  • Kim JJ, Funabiki F, Muramatsu H, Shibato K, Kim SH, Shiozaki H, Hatmannd H, Matsui M (2000). Negative solovatochromism of azo dyes derived from (dialkylamino) thiazole dimers. Chem Commun 9, 753– 754.
  • Kim JJ, Funabiki F, Muramatsu H, Shibato K, Kim SH, Shiozaki H, Hatmannd H, Matsui M (2001). Synthesis, structure, and UV–VIS absorption spectra of azo dyes derived from (dialkylamino) thiazole dimers. J Chem Soc Perkin Trans 2, 379–387.
  • Kobayashi S, Yokoyama H, Kamei H (1987). Substituent and solvent effects on electronic absorption spectra and thermal isomerization of push-pull-substituted cis- azobenzenes. Chem Phy Let 138, 333-338.
  • Masoud MS, Ali AE, Shaker MA, Ghani MA (2005). Solvent and substituent effects on spectroscopical changes of some diazoaminobenzene derivatives. Spectrochim Acta Part A: Molec and Biomol Spec 61, 3102-3107.
  • Matsui M, Joglekar B, Ishigure Y, Shibito K, Maramatsu H, Maruto Y (1993). Synthesis of 3-Cyano-6-hydroxy- 5-[2-(perfluoroalkyl)phenylazo]-2-pyridones and their application for dye diffusion thermal transfer printing. Bull Chem Soc Jpn 66, 1790-1794.
  • Mijin DZ, Ušćumlić GS, Perišić-Janjić NU, Valentić NV (2006). Substituent and solvent effects on the UV/vis absorption spectra of 5-(3- and 4-substituted arylazo)- 4,6-dimethyl-3-cyano-2-pyridones. Chem Phy Let 418, 223-229.
  • Qian Y, Wang G, Xiao G, Lin B, Cui Y (2007). The first- order molecular hyperpolarizability and thermal stability of charge-transfer azo diol and azo aldimine. Dyes and Pigments 75, 460-465.
  • Qui F, Cao Y, Xu H, Jiang Y, Zhou Y, Liu J (2007). Synthesis and properties of polymer containing azo-dye chromophores for nonlinear optical applications. Dyes and Pigments 75, 454-459.
  • Sıdır İ, Taşal E, Gülseven Y, Gungor T, Berber H, Oğretir C (2009). Studies on solvatochromic behavior of some monoazo derivatives using electronic absorption spectra. Int J Hydrogen Energy 34, 5267–5273.
  • So BK, Kim HJ, Lee SM, Song HH, Park JH (2006). Novel bent-shaped liquid crystalline compounds: IV. Dimesogenic compounds containing 2-hydroxy-1,3- dioxypropylene and azobenzene mesogens. Dyes Pigments 70, 38-42.
  • Ušćumlić GS, Mijin DZ, Valentić NV, Vajs VV, Sušić BM (2004). Substituent and solvent effects on the UV/Vis absorption spectra of 5-(4-substituted arylazo)-6- hydroxy-4-methyl-3-cyano-2-pyridones. Chem Phy Let 397, 148-153.
  • Valentic VN, Uscumlic SG, Radojkovic-Velickovic M (1999). Solvent effects on electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils. J Serb Chem Soc 64, 149–154.
  • Yıldırım S (2007). Synthesis of monoazo compounds of some substitiue anilin with benzene-1,3,5-triol and investigation of their tautomeric equilibrium, Msc Thesis, Anadolu University, Eskişehir, Turkey.
Year 2011, , 7 - 11, 23.12.2011
https://doi.org/10.17678/beuscitech.47153

Abstract

References

  • Aksu N (2007). Synthesis of monoazo compounds of some substitue anilin with benzene-1,3-diol and investigation of their tautomeric equilibrium, Msc Thesis, Anadolu University, Eskişehir, Turkey.
  • Bartkiewicz S, Matczyszyn K, Miniewicz A, Kajzar F (2001). High gain of light in photoconducting polymer– nematic liquid crystal hybrid structures. Opt Commun 187, 257-261.
  • Ermis E (2003). Bazı 2-substitue anilin ve benzen-1,3- diol ile monoazo bileşiklerinin sentezlenmesi. Master Thesis, Anadolu University, Fen Bilimleri Enstitusu, Eskişehir, Turkey.
  • Gibson WM, Shannon PJ, Shao-Tang S, Swetlin BJ (1991). Surface-mediated alignment of nematic liquid crystals with polarized laser light. Nature 351, 49-50.
  • Giménez R, Millaruelo H, Piňol M, Serrano JL, Viňuales A, Rosenhauer R, Fischer T, Stumpe J (2005). Synthesis, thermal and optical properties of liquid crystalline terpolymers containing azobenzene and dye moieties. Polymer 46, 9230-9242.
  • Gregory P (1991). High-technology applications of organic colorants plenum, New York.
  • Gülseven Y, Taşal E, Sıdır İ, Güngor T, Berber H, Öğretir C (2009). Solvatochromic effect studies on the absorption spectra of 4-(2-ethylphenyl) diazenyl) benzene-1,3-diol and 2-((2-ethylphenyl) diazenyl) benzene-1,3,5-triol molecules. Int J Hydrogen Energ 34, 5255-5259.
  • Gülseven Sıdır Y, Sıdır İ, Berber H, Taşal E (2011a). UV- spectral changes for some azo compounds in the presence of different solvents. J Mol Liq 162, 148–154.
  • Gülseven Sıdır Y, Sıdır İ, Taşal E, Ermiş E (2011b). Studies on the electronic absorption spectra of some monoazo derivatives. Spectrochim Acta Part A: Molec and Biomol Spectros 78, 640-647.
  • Hansch C, Leo A, Taft RW (1991). A Survey of Hammett Substituent Constants and Resonance and Field Parameters. Chem Rev 91, 165-195.
  • Issa RM, Assar SS, Dessouki HM (1992). Halochromic and electronic absorption spectral properties for some azo- azomethine dyes. Egyptian J Chem 35, 321-334.
  • Kim JJ, Funabiki F, Muramatsu H, Shibato K, Kim SH, Shiozaki H, Hatmannd H, Matsui M (2000). Negative solovatochromism of azo dyes derived from (dialkylamino) thiazole dimers. Chem Commun 9, 753– 754.
  • Kim JJ, Funabiki F, Muramatsu H, Shibato K, Kim SH, Shiozaki H, Hatmannd H, Matsui M (2001). Synthesis, structure, and UV–VIS absorption spectra of azo dyes derived from (dialkylamino) thiazole dimers. J Chem Soc Perkin Trans 2, 379–387.
  • Kobayashi S, Yokoyama H, Kamei H (1987). Substituent and solvent effects on electronic absorption spectra and thermal isomerization of push-pull-substituted cis- azobenzenes. Chem Phy Let 138, 333-338.
  • Masoud MS, Ali AE, Shaker MA, Ghani MA (2005). Solvent and substituent effects on spectroscopical changes of some diazoaminobenzene derivatives. Spectrochim Acta Part A: Molec and Biomol Spec 61, 3102-3107.
  • Matsui M, Joglekar B, Ishigure Y, Shibito K, Maramatsu H, Maruto Y (1993). Synthesis of 3-Cyano-6-hydroxy- 5-[2-(perfluoroalkyl)phenylazo]-2-pyridones and their application for dye diffusion thermal transfer printing. Bull Chem Soc Jpn 66, 1790-1794.
  • Mijin DZ, Ušćumlić GS, Perišić-Janjić NU, Valentić NV (2006). Substituent and solvent effects on the UV/vis absorption spectra of 5-(3- and 4-substituted arylazo)- 4,6-dimethyl-3-cyano-2-pyridones. Chem Phy Let 418, 223-229.
  • Qian Y, Wang G, Xiao G, Lin B, Cui Y (2007). The first- order molecular hyperpolarizability and thermal stability of charge-transfer azo diol and azo aldimine. Dyes and Pigments 75, 460-465.
  • Qui F, Cao Y, Xu H, Jiang Y, Zhou Y, Liu J (2007). Synthesis and properties of polymer containing azo-dye chromophores for nonlinear optical applications. Dyes and Pigments 75, 454-459.
  • Sıdır İ, Taşal E, Gülseven Y, Gungor T, Berber H, Oğretir C (2009). Studies on solvatochromic behavior of some monoazo derivatives using electronic absorption spectra. Int J Hydrogen Energy 34, 5267–5273.
  • So BK, Kim HJ, Lee SM, Song HH, Park JH (2006). Novel bent-shaped liquid crystalline compounds: IV. Dimesogenic compounds containing 2-hydroxy-1,3- dioxypropylene and azobenzene mesogens. Dyes Pigments 70, 38-42.
  • Ušćumlić GS, Mijin DZ, Valentić NV, Vajs VV, Sušić BM (2004). Substituent and solvent effects on the UV/Vis absorption spectra of 5-(4-substituted arylazo)-6- hydroxy-4-methyl-3-cyano-2-pyridones. Chem Phy Let 397, 148-153.
  • Valentic VN, Uscumlic SG, Radojkovic-Velickovic M (1999). Solvent effects on electronic absorption spectra of 3-N-(4-substituted phenyl)-5-carboxy uracils. J Serb Chem Soc 64, 149–154.
  • Yıldırım S (2007). Synthesis of monoazo compounds of some substitiue anilin with benzene-1,3,5-triol and investigation of their tautomeric equilibrium, Msc Thesis, Anadolu University, Eskişehir, Turkey.
There are 24 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Yadigar Gülseven Sidir This is me

Yadigar Gülseven Sıdır This is me

İsa Sidir This is me

Isa Sıdır This is me

Halil Berber

Halil Berber This is me

Erol Taşal This is me

Erol Tasal This is me

Publication Date December 23, 2011
Submission Date October 31, 2011
Published in Issue Year 2011

Cite

IEEE Y. G. Sidir, “An experimental study on relationship between hammett substituent constant and electronic absorption wavelength of some azo dyes”, Bitlis Eren University Journal of Science and Technology, vol. 1, no. 1, pp. 7–11, 2011, doi: 10.17678/beuscitech.47153.