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Investigating the halochromic properties of azo dyes in an aqueous environment by using a combined experimental and theoretical approach

(2012) CHEMISTRY-A EUROPEAN JOURNAL. 18(26). p.8120-8129
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HPC-UGent: the central High Performance Computing infrastructure of Ghent University
Abstract
The halochromism in solution of a prototypical example of an azo dye, ethyl orange, was investigated by using a combined theoretical and experimental approach. Experimental UV/Vis and Raman spectroscopy pointed towards a structural change of the azo dye with changing pH value (in the range pH 53). The pH-sensitive behavior was modeled through a series of ab initio computations on the neutral and various singly and doubly protonated structures. For this purpose, contemporary DFT functionals (B3LYP, CAM-B3LYP, and M06) were used in combination with implicit modeling of the water solvent environment. Static calculations were successful in assigning the most-probable protonation site. However, to fully understand the origin of the main absorption peaks, a molecular dynamics simulation study in a water molecular environment was used in combination with time-dependent DFT (TD-DFT) calculations to deduce average UV/Vis spectra that take into account the flexibility of the dye and the explicit interactions with the surrounding water molecules. This procedure allowed us to achieve a remarkable agreement between the theoretical and experimental UV/Vis spectrum and enabled us to fully unravel the pH-sensitive behavior of ethyl orange in aqueous environment.
Keywords
density functional calculations, pigments, azo compounds, dyes, SOLVATION MODELS, ELECTRON-DENSITY, BIOMOLECULAR SYSTEMS, TD-DFT, halochromism, UV, Vis spectroscopy, DENSITY-FUNCTIONAL THEORY, SPACE GAUSSIAN PSEUDOPOTENTIALS, PH-SENSITIVE FUNCTION, MOLECULAR-DYNAMICS, EXCITED-STATES, TEXTILE MATERIALS

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Chicago
De Meyer, Thierry, Karen Hemelsoet, Lien Van der Schueren, Ewald Pauwels, Karen De Clerck, and Veronique Van Speybroeck. 2012. “Investigating the Halochromic Properties of Azo Dyes in an Aqueous Environment by Using a Combined Experimental and Theoretical Approach.” Chemistry-a European Journal 18 (26): 8120–8129.
APA
De Meyer, Thierry, Hemelsoet, K., Van der Schueren, L., Pauwels, E., De Clerck, K., & Van Speybroeck, V. (2012). Investigating the halochromic properties of azo dyes in an aqueous environment by using a combined experimental and theoretical approach. CHEMISTRY-A EUROPEAN JOURNAL, 18(26), 8120–8129.
Vancouver
1.
De Meyer T, Hemelsoet K, Van der Schueren L, Pauwels E, De Clerck K, Van Speybroeck V. Investigating the halochromic properties of azo dyes in an aqueous environment by using a combined experimental and theoretical approach. CHEMISTRY-A EUROPEAN JOURNAL. 2012;18(26):8120–9.
MLA
De Meyer, Thierry, Karen Hemelsoet, Lien Van der Schueren, et al. “Investigating the Halochromic Properties of Azo Dyes in an Aqueous Environment by Using a Combined Experimental and Theoretical Approach.” CHEMISTRY-A EUROPEAN JOURNAL 18.26 (2012): 8120–8129. Print.
@article{2963923,
  abstract     = {The halochromism in solution of a prototypical example of an azo dye, ethyl orange, was investigated by using a combined theoretical and experimental approach. Experimental UV/Vis and Raman spectroscopy pointed towards a structural change of the azo dye with changing pH value (in the range pH 53). The pH-sensitive behavior was modeled through a series of ab initio computations on the neutral and various singly and doubly protonated structures. For this purpose, contemporary DFT functionals (B3LYP, CAM-B3LYP, and M06) were used in combination with implicit modeling of the water solvent environment. Static calculations were successful in assigning the most-probable protonation site. However, to fully understand the origin of the main absorption peaks, a molecular dynamics simulation study in a water molecular environment was used in combination with time-dependent DFT (TD-DFT) calculations to deduce average UV/Vis spectra that take into account the flexibility of the dye and the explicit interactions with the surrounding water molecules. This procedure allowed us to achieve a remarkable agreement between the theoretical and experimental UV/Vis spectrum and enabled us to fully unravel the pH-sensitive behavior of ethyl orange in aqueous environment.},
  author       = {De Meyer, Thierry and Hemelsoet, Karen and Van der Schueren, Lien and Pauwels, Ewald and De Clerck, Karen and Van Speybroeck, Veronique},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {density functional calculations,pigments,azo compounds,dyes,SOLVATION MODELS,ELECTRON-DENSITY,BIOMOLECULAR SYSTEMS,TD-DFT,halochromism,UV,Vis spectroscopy,DENSITY-FUNCTIONAL THEORY,SPACE GAUSSIAN PSEUDOPOTENTIALS,PH-SENSITIVE FUNCTION,MOLECULAR-DYNAMICS,EXCITED-STATES,TEXTILE MATERIALS},
  language     = {eng},
  number       = {26},
  pages        = {8120--8129},
  title        = {Investigating the halochromic properties of azo dyes in an aqueous environment by using a combined experimental and theoretical approach},
  url          = {http://dx.doi.org/10.1002/chem.201103633},
  volume       = {18},
  year         = {2012},
}

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