Synthesis and Evaluation of Changes Induced by Solvent and Substituent in Electronic Absorption Spectra of New Azo Disperse Dyes Containig Barbiturate Ring

Abstract

Six azo disperse dyes were prepared by diazotizing 4-amino hippuric acid and coupled with barbituric acid and 2-thiobarbituric acid. Then, the products were reacted with aromatic aldehyde, sodium acetate, and acetic anhydride, and oxazolone derivatives were formed. Characterization of the dyes was carried out by using UV-Vis, FT-IR,1H NMR and13C NMR, and mass spectroscopic techniques. The solvatochromic behavior of azo disperse dyes was evaluated in various solvents. The effects of substituents of aromatic aldehyde, barbiturate, and thiobarbiturate ring on the color of dyes were investigated.

A Feasible Method Applied to One-Bath Process of Wool/Acrylic Blended Fabrics with Novel Heterocyclic Reactive Dyes and Application Properties of Dyed Textiles

“…As observed in Table 1, the maximum absorption of dyes did not shift significantly, indicating that they did not have a strong solvent dependence. Meanwhile, the higher the polarity of the solvent, the further λmax was shifted towards a longer wavelength (bathochromism), which can be attributed to dye-solvent interactions by the dipolar effect [42] and intermolecular hydrogen bonding forces [43]. Further, the optical band gap was determined from the onset absorption edge λonset at higher wavelengths according to Equation (5) [44].…”

Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

“…The spectral data (Nujol mull) and magnetic moment values are summarized in Table . The spectrum of the ligand displays bands at 247, 288, 312; and 456 and 511 nm attributed to π–π* transitions of aromatic rings; and π–π* and n–π* transitions of the entire conjugated ligand . For the electronic spectra of all complexes, the π–π* and n–π* transitions shift slightly due to complexation.…”

“…Thiobarbiturates are some of most important pyrimidine derivatives, and 2‐thiobarbituric acid has been used in the pharmacological and analytical fields. Thiobarbiturates have been reported to have diverse biological activities, for example antimicrobial, antifungal, cell reinforcement, antidepressant, antitubercular and anti‐convulsant activities …”

Synthesis of pharmacological dyes and their application on synthetic fabrics

“…Barbituric acid derivatives are well known to exhibit strong biological activity, and so they have found numerous applications as pharmaceuticals. Barbiturates are a class of drugs that are utilised as anaesthetics and sleeping agents and for the treatment of anxiety, epilepsy, and other psychiatric disorders, and they possess effects on the motor and sensory functions . They are also widely used as valuable reagents in organic syntheses , as materials with special physical properties , and also as useful models for investigating mechanisms of important reactions of general chemical utility and also of enzymatic reactions .…”