A detailed UV-Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight
Abstract
Six donor-pi-acceptor azo dyes, with altered donor- (p-hydroxyphenyl-and naphthalene-2ol) and carboxylic based acceptor groups, were subjected to detailed solvatochromic and tautomeric investigation in different environments by experimental and theoretical approaches. Naphthalene2-ol compounds exhibit azo-hydrazone tautomerism in all solvents, wherein benzoic-and cinnamic acid-based compounds appear in solutions as a complex system of neutral forms and corresponding carboxylates. p-Hydroxyphenyl based compounds adopt the azo form in all investigated solvents. A special focus was placed on the definition of the anionic species and the extent of the deprotonation in different alkaline solutions. Excellent agreement between theoretical and experimental data is attained.
Keywords:
Azo&ndash / hydrazone equilibrium / Acid-base equilibrium / Solvatochromism / DFT analysis / Linear solvation energy relationships analysisSource:
Comptes Rendus Chimie, 2021, 24, 2, 267-+Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-MESTD-inst-2020-200026)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200135)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200287)
DOI: 10.5802/crchim.85
ISSN: 1631-0748
WoS: 000734063900018
Scopus: 2-s2.0-85110232701
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Inovacioni centarTY - JOUR AU - Matović, Luka AU - Lađarević, Jelena AU - Vitnik, Željko AU - Vitnik, Vesna AU - Mijin, Dušan PY - 2021 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4771 AB - Six donor-pi-acceptor azo dyes, with altered donor- (p-hydroxyphenyl-and naphthalene-2ol) and carboxylic based acceptor groups, were subjected to detailed solvatochromic and tautomeric investigation in different environments by experimental and theoretical approaches. Naphthalene2-ol compounds exhibit azo-hydrazone tautomerism in all solvents, wherein benzoic-and cinnamic acid-based compounds appear in solutions as a complex system of neutral forms and corresponding carboxylates. p-Hydroxyphenyl based compounds adopt the azo form in all investigated solvents. A special focus was placed on the definition of the anionic species and the extent of the deprotonation in different alkaline solutions. Excellent agreement between theoretical and experimental data is attained. T2 - Comptes Rendus Chimie T1 - A detailed UV-Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight EP - + IS - 2 SP - 267 VL - 24 DO - 10.5802/crchim.85 ER -
@article{ author = "Matović, Luka and Lađarević, Jelena and Vitnik, Željko and Vitnik, Vesna and Mijin, Dušan", year = "2021", abstract = "Six donor-pi-acceptor azo dyes, with altered donor- (p-hydroxyphenyl-and naphthalene-2ol) and carboxylic based acceptor groups, were subjected to detailed solvatochromic and tautomeric investigation in different environments by experimental and theoretical approaches. Naphthalene2-ol compounds exhibit azo-hydrazone tautomerism in all solvents, wherein benzoic-and cinnamic acid-based compounds appear in solutions as a complex system of neutral forms and corresponding carboxylates. p-Hydroxyphenyl based compounds adopt the azo form in all investigated solvents. A special focus was placed on the definition of the anionic species and the extent of the deprotonation in different alkaline solutions. Excellent agreement between theoretical and experimental data is attained.", journal = "Comptes Rendus Chimie", title = "A detailed UV-Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight", pages = "+-267", number = "2", volume = "24", doi = "10.5802/crchim.85" }
Matović, L., Lađarević, J., Vitnik, Ž., Vitnik, V.,& Mijin, D.. (2021). A detailed UV-Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight. in Comptes Rendus Chimie, 24(2), 267-+. https://doi.org/10.5802/crchim.85
Matović L, Lađarević J, Vitnik Ž, Vitnik V, Mijin D. A detailed UV-Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight. in Comptes Rendus Chimie. 2021;24(2):267-+. doi:10.5802/crchim.85 .
Matović, Luka, Lađarević, Jelena, Vitnik, Željko, Vitnik, Vesna, Mijin, Dušan, "A detailed UV-Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight" in Comptes Rendus Chimie, 24, no. 2 (2021):267-+, https://doi.org/10.5802/crchim.85 . .