1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure

Agnieszka Kudelko; Monika Olesiejuk; Marcin Luczynski; Marcin Swiatkowski; Tomasz Sieranski; Rafal Kruszynski

doi:10.3390/molecules25122822

1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure

Molecules. 2020 Jun 18;25(12):2822. doi: 10.3390/molecules25122822.

Authors

Agnieszka Kudelko¹, Monika Olesiejuk¹, Marcin Luczynski¹, Marcin Swiatkowski², Tomasz Sieranski², Rafal Kruszynski²

Affiliations

¹ Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, Poland.
² Department of X-ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, PL-90924 Łódź, Poland.

Abstract

Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by ¹H-NMR, ¹³C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.

Keywords: 2-arylazo-5-aryl-1,3,4-thiadiazoles; azo-coupling reactions; crystal structure; heterocycles.

MeSH terms

Azo Compounds / chemical synthesis*
Azo Compounds / chemistry*
Models, Molecular
Molecular Structure
Spectrophotometry, Ultraviolet
Thiadiazoles / chemistry*

Substances

Azo Compounds
Thiadiazoles
1,3,4-thiadiazole