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

Thierry De Meyer, Karen Hemelsoet UGent, Veronique Van Speybroeck UGent and Karen De Clerck UGent (2014) DYES AND PIGMENTS. 102. p.241-250
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
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)
journal title
DYES AND PIGMENTS
Dyes Pigment.
volume
102
pages
241 - 250
publisher
ELSEVIER SCI LTD
Web of Science type
Article
Web of Science id
000331483800031
JCR category
MATERIALS SCIENCE, TEXTILES
JCR impact factor
3.966 (2014)
JCR rank
1/22 (2014)
JCR quartile
1 (2014)
ISSN
0143-7208
DOI
10.1016/j.dyepig.2013.10.048
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
4353650
handle
http://hdl.handle.net/1854/LU-4353650
date created
2014-04-04 15:24:12
date last changed
2017-03-09 12:19:57
@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},
}

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.