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Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes

(2014) DYES AND PIGMENTS. 102. p.241-250
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Abstract
Sulfonphthaleine dyes are an important class of pH indicators, finding applications in novel (textile) sensors. In this paper, we present a combined experimental and theoretical study to elucidate the halochromic behaviour of a large set of sulfonphthaleine compounds. Starting from an experimental analysis consisting of UV-Vis spectroscopy, the pH region and the absorption wavelengths related to the colour shift are obtained and pK(a) values are derived. The effect of the substituents on the pH region can be traced back to their electron donating/withdrawing properties. Time-Dependent Density Functional Theory (TD-DFT) is able to adequately produce the trend in experimental wavelengths. Proton affinities are used to assess the effect of substituents on the pH region. The combination of theory and experiment is able to give a better understanding of the pH sensitivity; the methodology in this work will be useful in future dye design and is applicable to other dye classes as well. (C) 2013 Elsevier Ltd. All rights reserved.
Keywords
GLASSY-CARBON ELECTRODE, GENERALIZED-GRADIENT-APPROXIMATION, DENSITY-FUNCTIONAL THEORY, CONTINUUM SOLVATION METHODS, EXCITED-STATE PROPERTIES, AB-INITIO CALCULATIONS, COMPLETE BASIS-SET, TD-DFT, AZO DYES, THYMOL BLUE, Sulfonphthaleine dyes, Halochromism, TD-DFT, UV-Vis spectroscopy, Substituent effects, pK(a)

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Citation

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Chicago
De Meyer, Thierry, Karen Hemelsoet, Veronique Van Speybroeck, and Karen De Clerck. 2014. “Substituent Effects on Absorption Spectra of pH Indicators: An Experimental and Computational Study of Sulfonphthaleine Dyes.” Dyes and Pigments 102: 241–250.
APA
De Meyer, Thierry, Hemelsoet, K., Van Speybroeck, V., & De Clerck, K. (2014). Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes. DYES AND PIGMENTS, 102, 241–250.
Vancouver
1.
De Meyer T, Hemelsoet K, Van Speybroeck V, De Clerck K. Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes. DYES AND PIGMENTS. ELSEVIER SCI LTD; 2014;102:241–50.
MLA
De Meyer, Thierry, Karen Hemelsoet, Veronique Van Speybroeck, et al. “Substituent Effects on Absorption Spectra of pH Indicators: An Experimental and Computational Study of Sulfonphthaleine Dyes.” DYES AND PIGMENTS 102 (2014): 241–250. Print.
@article{4353650,
  abstract     = {Sulfonphthaleine dyes are an important class of pH indicators, finding applications in novel (textile) sensors. In this paper, we present a combined experimental and theoretical study to elucidate the halochromic behaviour of a large set of sulfonphthaleine compounds. Starting from an experimental analysis consisting of UV-Vis spectroscopy, the pH region and the absorption wavelengths related to the colour shift are obtained and pK(a) values are derived. The effect of the substituents on the pH region can be traced back to their electron donating/withdrawing properties. Time-Dependent Density Functional Theory (TD-DFT) is able to adequately produce the trend in experimental wavelengths. Proton affinities are used to assess the effect of substituents on the pH region. The combination of theory and experiment is able to give a better understanding of the pH sensitivity; the methodology in this work will be useful in future dye design and is applicable to other dye classes as well. (C) 2013 Elsevier Ltd. All rights reserved.},
  author       = {De Meyer, Thierry and Hemelsoet, Karen and Van Speybroeck, Veronique and De Clerck, Karen},
  issn         = {0143-7208},
  journal      = {DYES AND PIGMENTS},
  keyword      = {GLASSY-CARBON ELECTRODE,GENERALIZED-GRADIENT-APPROXIMATION,DENSITY-FUNCTIONAL THEORY,CONTINUUM SOLVATION METHODS,EXCITED-STATE PROPERTIES,AB-INITIO CALCULATIONS,COMPLETE BASIS-SET,TD-DFT,AZO DYES,THYMOL BLUE,Sulfonphthaleine dyes,Halochromism,TD-DFT,UV-Vis spectroscopy,Substituent effects,pK(a)},
  language     = {eng},
  pages        = {241--250},
  publisher    = {ELSEVIER SCI LTD},
  title        = {Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes},
  url          = {http://dx.doi.org/10.1016/j.dyepig.2013.10.048},
  volume       = {102},
  year         = {2014},
}

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