Synthesis of 5-azo-8-hydroxy-2-methylquinoline dyes and relevant spectroscopic, electrochemical and computational studies

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F17%3A00473739" target="_blank" >RIV/61388955:_____/17:00473739 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.dyepig.2017.03.043" target="_blank" >http://dx.doi.org/10.1016/j.dyepig.2017.03.043</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.dyepig.2017.03.043" target="_blank" >10.1016/j.dyepig.2017.03.043</a>

Result language
angličtina
Original language name
Synthesis of 5-azo-8-hydroxy-2-methylquinoline dyes and relevant spectroscopic, electrochemical and computational studies
Original language description
Twenty four derivatives of 5-azo-8-hydroxy-2-methylquinoline dyes with twenty three novel structures have been synthesized in an efficient one-pot synthesis protocol. Their properties were characterized by the combination of IR, NMR, MS, HRMS, GC-MS and electronic absorption spectroscopy. Two of the novel dyes have been synthesized as hydrochloride salts and structurally characterized by X-ray crystallography. The oxidation and reduction properties of selected 5-azo-8-hydroxy-2-methylquinoline dyes were studied using cyclic voltammetry. The measured visible absorption spectra of the dyes were discussed regarding the effects of substituent, varying pH and solvent upon their absorption ability. The molecular orbitals of the selected dyes have been calculated by density functional theory (DFT), which demonstrated that the HOMO orbitals were concentrated in the aromatic rings and in the azo part (–N=N–). The calculated HOMO and LUMO energies are in consistence with redox behavior of azoquinolines. The obtained dyes were successfully incorporated into polyester fabrics and their light fastness properties were evaluated.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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