Design, characterization, theoretical studies, and dyeing properties of new novel diazo salicylaldehyde Schiff base catalyzed with ceric (IV) ammonium nitrate (CAN) as an eco-friendly catalyst

Abstract

Purpose The paper aims to the preparation of novel disperse dye based on azo salicylaldehyde derivatives TF-A [2-hydroxy-5-((3-(trifluoromethyl)phenyl)diazenyl)benzaldehyde] and full evaluation of their use as disperse dye TF-ASC [bis 2-hydroxy-5-((3-(trifluoromethyl)phenyl)diazenyl)benzaldehyde Schiff base with 4,4'-methylenedianiline] for dyeing polyester fabric at various conditions. Design/methodology/approach The dispersed dye was synthesized via Schiff base condensation in the presence of ceric ammonium nitrate cerium ammonium nitrate 10 mmole% as an eco-friendly catalyst at room temperature. The chemical structure of the prepared dye was characterized via elemental analysis, Fourier-transform infrared spectroscopy, 1H- and 13 C-NMR spectroscopic analysis tools. This study thoroughly examined the dyeing of disperse dye TF-ASC on polyester at various conditions. The characteristics of dyed polyester fabric were measured by colour measurements, as well as light, washing, crock fastness and finally, colour strength. The discrete fourier transform (DFT) theoretical studies, including EHOMO, ELUMO and optimized geometrical structure, were assumed and discussed in detail. Findings The results showed that the synthesized organic dye TF-ASC was highly functional and appropriate for this kind of dyeing method. The dyeing fabrics obtained from disperse dye TF-ASC, properties possess high colour strength as well as good overall fastness properties. These dyes had a high affinity for polyester fabric, with just a tiny change in dye affinity when the pH was changed, even under alkaline circumstances. The dye levelness and shade depth of the colour results were good, and there were a variety of hues from light brownish yellow to deep brownish yellow. The results obtained from DFT computational studies such as EHOMO, ELUMO, optimized structure, diploe moment µ and electrophilicity index deduced that prepared organic dye TF-ASC is more applicable as a dispersed dye. Originality/value This research is significant because it provides a new dye for dyeing polyethylene terephthalate fibres with exceptional brightness and levelness; the method of preparation is a useful pathway due to its being known as a green chemistry method.

Design, green synthesis, and quorum sensing quenching potential of novel 2-oxo-pyridines containing a thiophene/furan scaffold and targeting a LasR gene on P. aeruginosa

“…The advantage of the reaction in the case of using CAN as a catalyst is that the reaction has occurred by stirring at room temperature for a short time and with good yield compared to the other hazardous methods. 54–56…”

“…The advantage of the reaction in the case of using CAN as a catalyst is that the reaction has occurred by stirring at room temperature for a short time and with good yield compared to the other hazardous methods. [54][55][56] Treatment of 1,6-diamino-2-oxo-pyridine derivatives 1a,b with different aldehydes such as 4-ethoxybenzaldehyde, 5bromo-2-hydroxybenzaldehyde, 2-hydroxynaphthaldehyde, and 9-anthraldehyde in either reuxing solution in the presence of acid catalyst (acetic acid) or stirring the solution in the presence of cerium ammonium nitrate at room temperature to produce the corresponding Schiff base derivatives 2a,b, 3a,b, 4a,b, and 5a,b, respectively (Scheme 1). The structures of Schiff base derivatives were conrmed using elemental (CHN) and spectral analysis (IR, 1 H NMR, and 13 C NMR).…”

One-pot synthesis of pyrazolo[4,3-d]thiazole derivatives containing α-aminophosphonate as potential Mur A inhibitors against MDR pathogens with radiosterilization and molecular modeling simulation

“…A molecule's ability to donate electrons is represented by E HOMO , whereas its ability to accept electrons is represented by E LUMO . 58,59 For developing the concept of binding systems for drugs and receptors, the most active amino phosphonate derivative 5a exhibited that the HOMO is mainly localized over pyrazolo [4,3-d]thiazole nucleus and methyl amine at C2 of pyrazolo [4,3-d]thiazole, while for amino phosphonate derivative 5b distributed over benzylidene derivatives and the amino group of pyrazolo [4,3-d]thiazole moiety, indicating that these positions have high negative charges and therefore expected to be active sites and interacted with positively charged sites in the biological target. However, the LUMO orbitals for most active 5a and 5b were primarily concentrated on the pyrazole skeleton, N1-phenyl of pyrazole, and 4-nitrol phenyl at C3 of the pyrazolo [4,3-d]thiazole fragment slightly distributed over the thiazole core.…”