| Titre : |
Solvatochromism, halochromism, and azo–hydrazone tautomerism in novel V-shaped azo-azine colorants |
| Type de document : |
texte imprimé |
| Auteurs : |
Amol S. Choudhari, Auteur ; Sharad R. Patil, Auteur ; Nagaiyan Sekar, Auteur |
| Année de publication : |
2016 |
| Article en page(s) : |
p. 387-398 |
| Note générale : |
Bibliogr. |
| Langues : |
Anglais (eng) |
| Catégories : |
Colorants -- Analyse
Colorants azoïques
Halochromisme
Solvatochromisme
Tautomères
Tautomérie
|
| Index. décimale : |
667.3 Teinture et impression des tissus |
| Résumé : |
The azo–hydrazone tautomerism, solvatochromism, and halochromism in four novel V-shaped asymmetrical acceptor-?-donor-?-acceptor (A-?-D-?-A) compounds were examined. They contain 2,7,15,16-functionalised benzophenazine cores connected to the anchoring electron-deficient phenyl core via azo linkers and 2,7-position fused with anthraquinone. These compounds derived from 2-hydroxy-1,4-napthaquinone (lawsone) have been prepared in moderate to good yields. The synthesis involved the diazotisation of substituted aromatic amines, coupling onto 2-hydroxy-1,4-napthaquinone, and further condensing the resulting azo compounds with 1,2-diaminoanthraquinone in acetic acid. The absorption wavelengths of the dyes in different solvents were in the range 500–720 nm. The spectral changes of the synthesised azo-azine compounds in different pH indicated the formation of hydrazone tautomer in acidic pH and of azo tautomer in alkaline pH. Density functional theory was used to assess the tautomers in terms of geometry and position of the tautomeric equilibrium. Time-dependent density functional theory calculations allowed us to assign the electronic transitions (>90%) of the low-energy bands. |
| Note de contenu : |
- EXPERIMENTAL : Materials and instrumentation - Synthesis strategy - Computational details - Synthesis and characterisation
- RESULTS AND DISCUSSION : Photophysical properties - Structural effects - Halochromism - Electrochemical properties - Thermal stability - Optimised geometries of dyes 15 and 18 - Electronic vertical excitation spectra (TDDFT) |
| DOI : |
10.1111/cote.12226 |
| En ligne : |
https://drive.google.com/file/d/1YGoI2-lkk5G1Ew6QERMfvPbApGUckdyM/view?usp=drive [...] |
| Format de la ressource électronique : |
Pdf |
| Permalink : |
https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=27227 |
in COLORATION TECHNOLOGY > Vol. 132, N° 5 (10/2016) . - p. 387-398
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Solvatochromism, halochromism, and azo–hydrazone tautomerism in novel V-shaped azo-azine colorants in COLORATION TECHNOLOGY, Vol. 132, N° 5 (10/2016)
