A detailed UV–Vis spectral investigation of six azo dyes derived from benzoic- and cinnamic acids: experimental and theoretical insight

Autor: Matović, Luka, Lađarević, Jelena, Vitnik, Željko, Vitnik, Vesna, Mijin, Dušan
Jazyk: English<br />French
Rok vydání: 2021
Předmět:
Zdroj: Comptes Rendus. Chimie, Vol 24, Iss 2, Pp 267-280 (2021)
Druh dokumentu: article
ISSN: 1878-1543
DOI: 10.5802/crchim.85
Popis: Six donor–${\pi }$–acceptor azo dyes, with altered donor- (p-hydroxyphenyl- and naphthalene-2-ol) and carboxylic based acceptor groups, were subjected to detailed solvatochromic and tautomeric investigation in different environments by experimental and theoretical approaches. Naphthalene-2-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.
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