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Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones

Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona

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2010
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Authors
Alimmari, Adel SA
Marinković, Aleksandar D.
Mijin, Dušan
Valentić, Nataša V.
Todorović, Nina
Ušćumlić, Gordana
Article (Published version)
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Abstract
A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.
Serija novih piridonskih arilazo boja je sintetisana reakcijom odgovarajućih diazonijum soli i 3-cijano-4,6-difenil-2-piridona primenom klasične sinteze azo jedinjenja. Struktura sintetisanih boja je potvrđena na osnovu podataka dobijenih iz UV, FT-IR i 1H-NMR spektara. Solvatohromna svojstva boja su procenjena u odnosu na njihovu apsorpciju u vidljivom delu spektra u različitim rastvračima. Efekti rastvarača, dipolarnost/polarizabilnost i vodonične interakcije rastvarač/rastvorak, su analizirane primenom linearne korelacije solvatohromnih efekata predložene od strane Kamlet-a i Taft-a. Tautomerna ravnoteža 2-piridon/2-hidroksipiridin zavisi kako od efekata supstituenta tako i od uticaja rastvarača.
Keywords:
arylazo pyridone dyes / absorption spectra / solvent effect / substituent effect / tautomeric equilibration
Source:
Journal of the Serbian Chemical Society, 2010, 75, 8, 1019-1032
Publisher:
  • Serbian Chemical Society
Projects:
  • Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-142063)

DOI: 10.2298/JSC091009074A

ISSN: 0352-5139

WoS: 000281683900001

Scopus: 2-s2.0-77956426927
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/712
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IHTM

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