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Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study

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Quantitative_structure-activity_acc_2016.pdf (489.5Kb)
Authors
Dostanić, Jasmina
Lončarević, Davor
Zlatar, Matija
Vlahović, Filip
Jovanović, Dušan M.
Article (Accepted Version)
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Abstract
A series of arylazo pyridone dyes was synthesized by changing the type of the substituent group in the diazo moiety, ranging from strong electron-donating to strong electron-withdrawing groups. The structural and electronic properties of the investigated dyes was calculated at the M062X/6-31 + G(d,p) level of theory. The observed good linear correlations between atomic charges and Hammett sigma(p) constants provided a basis to discuss the transmission of electronic substituent effects through a dye framework. The reactivity of synthesized dyes was tested through their decolorization efficiency in TiO2 photocatalytic system (Degussa P-25). Quantitative structure activity relationship analysis revealed a strong correlation between reactivity of investigated dyes and Hammett substituent constants. The reaction was facilitated by electron-withdrawing groups, and retarded by electron-donating ones. Quantum mechanical calculations was used in order to describe the mechanism of the photocatal...ytic oxidation reactions of investigated dyes and interpret their reactivities within the framework of the Density Functional Theory (DFT). According to DFT based reactivity descriptors, i.e. Fukui functions and local softness, the active site moves from azo nitrogen atom linked to benzene ring to pyridone carbon atom linked to azo bond, going from dyes with electron-donating groups to dyes with electron-withdrawing groups.

Keywords:
Arylazo pyridone dyes / Substituent effect / Photocatalysis / Hammett equation / DFT-ab initio calculations / Fukui functions
Source:
Journal of Hazardous Materials, 2016, 316, 26-33
Publisher:
  • Elsevier Science Bv, Amsterdam
Funding / projects:
  • Nanostructured Functional and Composite Materials in Catalytic and Sorption Processes (RS-45001)
Note:
  • This is peer-reviewed version of the following article: Dostanić, J.; Lončarević, D.; Zlatar, M.; Vlahović, F.; Jovanović, D. M. Quantitative Structure-Activity Relationship Analysis of Substituted Arylazo Pyridone Dyes in Photocatalytic System: Experimental and Theoretical Study. J. Hazard. Mater. 2016, 316, 26–33. https://doi.org/10.1016/j.jhazmat.2016.05.015
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3584

DOI: 10.1016/j.jhazmat.2016.05.015

ISSN: 0304-3894

PubMed: 27209516

WoS: 000379564700004

Scopus: 2-s2.0-84968867079
[ Google Scholar ]
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URI
https://cherry.chem.bg.ac.rs/handle/123456789/3579
Collections
  • Publikacije
Institution/Community
Inovacioni centar
TY  - JOUR
AU  - Dostanić, Jasmina
AU  - Lončarević, Davor
AU  - Zlatar, Matija
AU  - Vlahović, Filip
AU  - Jovanović, Dušan M.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3579
AB  - A series of arylazo pyridone dyes was synthesized by changing the type of the substituent group in the diazo moiety, ranging from strong electron-donating to strong electron-withdrawing groups. The structural and electronic properties of the investigated dyes was calculated at the M062X/6-31 + G(d,p) level of theory. The observed good linear correlations between atomic charges and Hammett sigma(p) constants provided a basis to discuss the transmission of electronic substituent effects through a dye framework. The reactivity of synthesized dyes was tested through their decolorization efficiency in TiO2 photocatalytic system (Degussa P-25). Quantitative structure activity relationship analysis revealed a strong correlation between reactivity of investigated dyes and Hammett substituent constants. The reaction was facilitated by electron-withdrawing groups, and retarded by electron-donating ones. Quantum mechanical calculations was used in order to describe the mechanism of the photocatalytic oxidation reactions of investigated dyes and interpret their reactivities within the framework of the Density Functional Theory (DFT). According to DFT based reactivity descriptors, i.e. Fukui functions and local softness, the active site moves from azo nitrogen atom linked to benzene ring to pyridone carbon atom linked to azo bond, going from dyes with electron-donating groups to dyes with electron-withdrawing groups.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Hazardous Materials
T1  - Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study
VL  - 316
SP  - 26
EP  - 33
DO  - 10.1016/j.jhazmat.2016.05.015
UR  - Kon_3093
ER  - 
@article{
author = "Dostanić, Jasmina and Lončarević, Davor and Zlatar, Matija and Vlahović, Filip and Jovanović, Dušan M.",
year = "2016",
abstract = "A series of arylazo pyridone dyes was synthesized by changing the type of the substituent group in the diazo moiety, ranging from strong electron-donating to strong electron-withdrawing groups. The structural and electronic properties of the investigated dyes was calculated at the M062X/6-31 + G(d,p) level of theory. The observed good linear correlations between atomic charges and Hammett sigma(p) constants provided a basis to discuss the transmission of electronic substituent effects through a dye framework. The reactivity of synthesized dyes was tested through their decolorization efficiency in TiO2 photocatalytic system (Degussa P-25). Quantitative structure activity relationship analysis revealed a strong correlation between reactivity of investigated dyes and Hammett substituent constants. The reaction was facilitated by electron-withdrawing groups, and retarded by electron-donating ones. Quantum mechanical calculations was used in order to describe the mechanism of the photocatalytic oxidation reactions of investigated dyes and interpret their reactivities within the framework of the Density Functional Theory (DFT). According to DFT based reactivity descriptors, i.e. Fukui functions and local softness, the active site moves from azo nitrogen atom linked to benzene ring to pyridone carbon atom linked to azo bond, going from dyes with electron-donating groups to dyes with electron-withdrawing groups.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Hazardous Materials",
title = "Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study",
volume = "316",
pages = "26-33",
doi = "10.1016/j.jhazmat.2016.05.015",
url = "Kon_3093"
}
Dostanić, J., Lončarević, D., Zlatar, M., Vlahović, F.,& Jovanović, D. M.. (2016). Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study. in Journal of Hazardous Materials
Elsevier Science Bv, Amsterdam., 316, 26-33.
https://doi.org/10.1016/j.jhazmat.2016.05.015
Kon_3093
Dostanić J, Lončarević D, Zlatar M, Vlahović F, Jovanović DM. Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study. in Journal of Hazardous Materials. 2016;316:26-33.
doi:10.1016/j.jhazmat.2016.05.015
Kon_3093 .
Dostanić, Jasmina, Lončarević, Davor, Zlatar, Matija, Vlahović, Filip, Jovanović, Dušan M., "Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study" in Journal of Hazardous Materials, 316 (2016):26-33,
https://doi.org/10.1016/j.jhazmat.2016.05.015 .,
Kon_3093 .

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