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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Dyes and Pigments

ISSN

0143-7208

e-ISSN

—

Svazek periodika

142

Číslo periodika v rámci svazku

JUL 2017

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

16

Strana od-do

277-292

Kód UT WoS článku

000401393100038

EID výsledku v databázi Scopus

2-s2.0-85016320928