Phenylazoindole dyes 2: The molecular structure characterizations of new phenylazo indoles derived from 1,2-dimethylindole

被引:9
作者
Babur, Banu [1 ]
Seferoglu, Nurgul [2 ]
Aktan, Ebru [1 ]
Hokelek, Tuncer [3 ]
Sahin, Ertan [4 ]
Seferoglu, Zeynel [1 ]
机构
[1] Gazi Univ, Dept Chem, TR-06500 Ankara, Turkey
[2] Gazi Univ, TR-06500 Ankara, Turkey
[3] Hacettepe Univ, Dept Phys, TR-06800 Ankara, Turkey
[4] Ataturk Univ, Dept Chem, Erzurum, Turkey
关键词
Azo dyes; Phenylazo indoles; X-ray; DFT; Substituent effect; UV-vis; DENSITY-FUNCTIONAL THEORY; X-RAY-DIFFRACTION; AZO DYES; DISPERSE DYES; CONTINUUM; RAMAN;
D O I
10.1016/j.dyepig.2013.11.019
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this study, five new phenylazo indoles derived from 1,2-dimethylindole were synthesized and characterized to evaluate the substituent effects on the molecular structures and absorption spectra. Theoretical calculations were carried out by density functional theory. The experimental and theoretical results are compared. X-ray single-crystal diffraction analyses reveal that the dyes have similar planar molecular conformation between azo and aromatic/heteroaromatic ring units but dissimilar crystal packing. The analysis of the electronic spectra showed that the electron-withdrawing groups (-Cl and -CN) were more effective than the electron-donating groups (-CH3 and -OCH3). Dyes containing electron-donating groups do not show significant changes relative to the parent dye, whereas the absorption maxima move to longer wavelengths for dyes containing electron-withdrawing groups. In addition, the absorption maxima exhibit the little bathochromic shifts for each dye with the increasing dielectric constants of the solvents. (C) 2013 Published by Elsevier Ltd.
引用
收藏
页码:62 / 70
页数:9
相关论文
共 37 条
[1]   The synthesis, characterisation and molecular structure of a new hetarylazoindole dye studied by X-ray diffraction, spectral analysis and density functional theory calculation [J].
Aktan, Ebru ;
Seferoglu, Zeynel ;
Hokelek, Tuncer ;
Sahin, Ertan .
COLORATION TECHNOLOGY, 2012, 128 (05) :371-377
[2]   Synthesis and structure of a novel hetarylazoindole dye studied by X-ray diffraction, FT-IR, FT-Raman, UV-vis, NMR spectra and DFT calculations [J].
Aktan, Ebru ;
Babur, Banu ;
Seferoglu, Zeynel ;
Hokelek, Tuncer ;
Sahin, Ertan .
JOURNAL OF MOLECULAR STRUCTURE, 2011, 1002 (1-3) :113-120
[3]  
Annen O., 1987, Rev. Prog. Coloration, V17, P72
[4]  
[Anonymous], 1989, Review of Progress in Coloration and Related Topics
[5]  
[Anonymous], DYES PIGM
[6]  
[Anonymous], 1978, ADV QUANTUM CHEM
[7]  
[Anonymous], COLOR CHEM SYNTHESIS
[9]   Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory [J].
Bauernschmitt, R ;
Ahlrichs, R .
CHEMICAL PHYSICS LETTERS, 1996, 256 (4-5) :454-464
[10]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652