Synthesis and comparative solvatochromic studies of novel Mono azo ureido/thioureido benzimidazole dyes

Abstract

Purpose

This paper aims to synthesize new benzimidazole dyes aiming to study the solvent effects on their absorption in Ultraviolet-visible spectra.

Design/methodology/approach

Ureido/thioureido hydrazonamide benzimidazoles (U/THB) are prepared by condensation of N-aryl-1H-benzo[d]imidazole-2-carbohydrazonoyl bromides with ureido and/ or thioureido reagents. The target products are fully characterized for structural elucidation by means of their spectral and elemental methods. Solvatochromic behavior of U/THB dyes has been studied in different polar protic solvents at room temperature.

Findings

The absorption spectra distinguish two main bands at (350 nm–442 nm) and (308 nm–382 nm) referring to n-π* and π- π* transitions of the azo groups. Dimethyl formamide induces an extremely bathochromic transition comparing to the other protic solvents. The observed bathochromic shifts indicate strong interaction with solvents in the excited state. Most dyes show one absorbance in all solvents used, so they may exist in a single tautomeric form (hydrazo form).

Research limitations/implications

In the present paper, the synthesis of U/THB dyes was achieved by a simple and convenient pathway. In addition, the variations in substituents attached to the chromophoric moiety could also be studied.

Practical implications

The new U/THB dyes are accountable for providing good knowledge about their solvation and spectral properties of an order acceptable for industrial utilization.

Social implications

Synthesis of these new benzimidazole derivatives and study of their solvation and spectral properties provides good knowledge, which is very useful in many industrial applications (e.g. dye-sensitized solar cell, etc.).

Originality/value

The synthesized mono azo U/THB dyes are novel members in the benzimidazole family, where no details regarding the synthesis of such dyes are reported before in the literature. They are superior in terms of preparation, multiple applications and spectral properties.

Citation

Khalifa, M.E., Gobouri, A.A., Mahmoud, M.H.H., Almalki, A.S. and Kabli, F.M. (2022), "Synthesis and comparative solvatochromic studies of novel Mono azo ureido/thioureido benzimidazole dyes", Pigment & Resin Technology, Vol. 51 No. 3, pp. 290-300. https://doi.org/10.1108/PRT-03-2021-0027