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

0473739 - ÚFCH JH 2018 RIV GB eng J - Článek v odborném periodiku
Szala, M. - Nycz, J. E. - Malecki, G. J. - Sokolová, Romana - Ramešová, Šárka - Switlicka-Olszewska, A. - Strzelcyk, R. - Podsiadly, R. - Machura, B.
Synthesis of 5-azo-8-hydroxy-2-methylquinoline dyes and relevant spectroscopic, electrochemical and computational studies.
Dyes and Pigments. Roč. 142, JUL 2017 (2017), s. 277-292. ISSN 0143-7208. E-ISSN 1873-3743
Institucionální podpora: RVO:61388955
Klíčová slova: Density functional theory * X ray crystallography * Chemical analysis
Obor OECD: Physical chemistry
Impakt faktor: 3.767, rok: 2017

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.
Trvalý link: http://hdl.handle.net/11104/0270881