Disazo dyes containing pyrazole and indole moieties: Synthesis, characterization, absorption characteristics, theoretical calculations, structural and electronic properties

Autor: Tahir Tilki, Yeşim Kara, Merve Gökalp, İzzet Kara, Çiğdem Karabacak Atay, Fikret Karcı
Rok vydání: 2016
Předmět:
Structural and electronic properties
Absorption spectroscopy
Azo dyes
Visible absorption spectra
Spectroscopic analysis
010402 general chemistry
Photochemistry
01 natural sciences
Charge transfer
Electronic and optical properties
Materials Chemistry
Molecule
Electronic property
Chemical analysis
NBO analysis
Spectroscopic property
Physical and Theoretical Chemistry
Lone pair
Diazo coupling reaction
Nuclear magnetic resonance spectroscopy
Spectroscopy
Optical properties
010405 organic chemistry
Chemistry
Chemical shift
Solvatochromism
Chemical bonds
Condensed Matter Physics
Polycyclic aromatic hydrocarbons
Atomic and Molecular Physics
and Optics
0104 chemical sciences
Electronic
Optical and Magnetic Materials
Indole
Diazo couplings
Electronic properties
Absorption characteristics
Proton NMR
Physical chemistry
Complexation
Quantum chemistry
Natural bond orbital
Zdroj: Journal of Molecular Liquids. 215:647-655
ISSN: 0167-7322
DOI: 10.1016/j.molliq.2016.01.031
Popis: The newly synthesized thirteen disperse disazo dyes 3a-3m were prepared by diazotization of 5-amino-4-arylazo-3-methyl-1H-pyrazoles 2a-2m and coupling with 2-methyl indole. Their structures were characterized by UV-vis, FT-IR, H-1 NMR and elemental analysis. Solvatochromic properties in different solvents were studied. Also, the effects of acid and base on the visible absorption spectra of the dyes were informed. Besides, the theoretical vibrational frequencies have been scaled and compared with the corresponding experimental data. H-1 NMR spectra were recorded and chemical shifts of the molecules were compared to TMS by using the Gauge Independent Atomic Orbital (MO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy and dipole moment is performed using DFT method. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. All spectroscopic properties examined with the experimental techniques were supported with the computed results. (C) 2016 Elsevier B.V. All rights reserved.
Databáze: OpenAIRE
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