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Journal of Chemistry
Volume 2017, Article ID 8659346, 10 pages
https://doi.org/10.1155/2017/8659346
Research Article

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

Faculty of Science, Department of Chemistry, Gazi University, Teknikokullar, 06500 Ankara, Turkey

Correspondence should be addressed to Ebru Aktan; rt.ude.izag@natkaurbe

Received 3 January 2017; Accepted 22 February 2017; Published 4 April 2017

Academic Editor: James W. Gauld

Copyright © 2017 Ebru Aktan and Tahsin Uyar. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

In this study, the synthesized coupling component 1-(2-benzothiazolyl)-3-methylpyrazol-5-one reacted with diazotised heterocyclic amines to afford six novel hetarylazopyrazolone dyes. These azo dyes based on benzothiazole and benzimidazole ring systems were characterized by spectral methods and elemental analyses. The solvatochromic behaviors of these dyes in various solvents were evaluated. The ground state geometries of the dyes were optimized using density functional theory (DFT). Solvent, acid-base, and substituent influences on the wavelength of the maximum absorption were examined in detail. Time-dependent density functional theory (TD-DFT) calculations were performed to obtain the absorption spectra of the dyes in various solvents and the results compared with experimental values. Besides, frontier molecular orbitals (FMO) analysis for the dyes is also described from the computational process.