Quantitative structure-activity relationship analysis of substituted arylazo pyridone dyes in photocatalytic system: Experimental and theoretical study
Само за регистроване кориснике
2016
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Arylazo pyridone dyes / Substituent effect / Photocatalysis / Hammett equation / DFT-ab initio calculations / Fukui functionsИзвор:
Journal of Hazardous Materials, 2016, 316, 26-33Издавач:
- Elsevier
Финансирање / пројекти:
- Наноструктурни функционални и композитни материјали у каталитичким и сорпционим процесима (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-45001)
Напомена:
- The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/2910
DOI: 10.1016/j.jhazmat.2016.05.015
ISSN: 0304-3894
PubMed: 27209516
WoS: 000379564700004
Scopus: 2-s2.0-84968867079
Институција/група
IHTMTY - JOUR AU - Dostanić, Jasmina AU - Lončarević, Davor AU - Zlatar, Matija AU - Vlahović, Filip AU - Jovanović, Dušan M. PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1851 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 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 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", 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" }
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., 316, 26-33. https://doi.org/10.1016/j.jhazmat.2016.05.015
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 .
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 . .