title: Novel acid mono azo dye compound: synthesis, characterization, vibrational, optical and theoretical investigations of 2-[(E)-(8-hydroxyquinolin-5-yl)-diazenyl]-4,5-dimethoxybenzoic acid.
abstract: Novel acid mono azo dye, 2-[(E)-(8-hydroxyquinolin-5yl)-diazenyl]-4,5-dimethoxybenzoic acid (HQD), was synthesized by coupling diazonium salt solution of 2-amino-4,5-dimethoxybenzoic acid (DMA) with 8-hydroxyquinoline (HQ). This dye was characterized by UV-vis, IR & Raman, (1)H and (13)C NMR spectroscopic techniques and elemental analysis. The normal coordinate analysis of HQD was also performed to assign each band in vibrational spectra. DFT (B3LYP and B3PW91) calculations were employed to optimize the geometry, to interpret NMR spectra, to calculate and to determine the stable tautomeric structure of the compound. Natural Bond Orbital (NBO) analysis was performed to investigate intramolecular interactions. The vibrational spectral data obtained from solid phase IR & Raman spectra were assigned based on the results of the theoretical calculations. UV-vis spectroscopic technique was employed to obtain the optical band gap of HQD. The analysis of the optical absorption data revealed the existence of direct and indirect transitions in the optical band gaps. The optical band gaps of HQD have been found 1.95 and 1.90eV for direct and indirect transitions, respectively.
authors: Bozok University, Faculty of Arts and Sciences, Department of Chemistry, Yozgat, Turkey. msacmaci@hotmail.com
authors: Mustafa
authors: M
authors: Saçmacı
authors: Hatice Kanbur
authors: HK
authors: Cavuş
authors: Hatice
authors: H
authors: Arı
authors: Recep
authors: R
authors: Sahingöz
authors: Talat
authors: T
authors: Ozpozan
mesh_terms: D000143:Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry*; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D055620:Optical Phenomena; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D013237:Stereoisomerism; D013816:Thermodynamics; D014732:Vibration
chemical_list: C578117:2-((E)-(8-hydroxyquinolin-5-yl)-diazenyl)-4,5-dimethoxybenzoic acid; D000143:Acids; D001391:Azo Compounds; D001565:Benzoates; D004396:Coloring Agents; D006835:Hydrazones; D011804:Quinolines