Synthesis and Spectroscopic Characterization of Water Soluble Triazene Dyes Based on Glyco-conjugated Pyrazolone Derivat
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ORIGINAL ARTICLE
Synthesis and Spectroscopic Characterization of Water Soluble Triazene Dyes Based on Glyco‑conjugated Pyrazolone Derivatives Catalyzed by an Acidic Ionic Liquid Supported on Silica‑Coated Magnetite Nanoparticles Jalal Isaad1,2 · Ahmida El Achari3 Received: 28 April 2020 / Accepted: 11 September 2020 © The Tunisian Chemical Society and Springer Nature Switzerland AG 2020
Abstract Novel water soluble triazene dyes based on glyco-conjugated pyrazolone amines were synthetized by using N-propyl2-pyrrolidonium hydrogen sulfate supported on silica-coated magnetite nanoparticle as acid catalyst. This organic–inorganic hybrid composite showed an excellent catalytic activity toward diazotization reaction of pyrazolone amines performing triazene dyes under solvent-free conditions in high yields. The spectroscopic properties confirmed the tendency of these dyes to exist in their hydrazo-keto tautomer forms. The study of the solubility of these dyes in water showed that their water solubility requires a minimum percentage weight of 50% of the carbohydrate part. Graphic Abstract
Keywords Triazene · Pyrazolone · Carbohydrate · Nanoparticle · Water · Synthesis
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s42250-020-00186-9) contains supplementary material, which is available to authorized users. * Jalal Isaad [email protected] 1
Faculté des Sciences & Techniques d’Al Hoceima, Laboratoire R&D en sciences de l’ingénieur, BP 34, 32003 Ajdir, Morocco
2
Université Abdelmalek Essaâdi, Quartier M’haneche II, Avenue Palestine, B.P. 2117, Tétouan, Morocco
3
Engineering and Textile Materials Laboratory, Lille, Lille Nord de France University, 2 Allée Louise et Victor Champier, 59100 Roubaix, France
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Chemistry Africa
1 Introduction
in the diazotization of aromatic amine at low temperature to the corresponding diazonium salt, which reacts with an electron rich aromatic nucleophile [26]. The main disadvantage of this methodology is the use of toxic organic solvents, which cause environmental pollution and are not eco-friendly [27]. Therefore, there is still demand for simple methodologies to prepare triazene derivatives with more efficiency and shorter reaction time. To overcome these environmental limitations, hybrid materials can be considered as an important alternative due to their uses in different applications [28–31], and especially as green heterogeneous catalysts for numerous reactions [32–36]. Recently, we developed an acidic ionic liquid based on N-propyl-2-pyrrolidonium hydrogen sulfate ([HNMP]HSO4) moiety, supported on silica-coated magnetite nanoparticles “Fe3O4@SILnP” (Fig. 1) as a green catalyst for one-step diazotization-halogenation reaction of amines derivatives [37] and the synthesis of azoic dyes under solvent-free conditions [38]. Fe3O4@SILnP catalyst [37, 38] was selected because it provides a large surface area and
Triazene derivatives are considered as polyazoic compounds containing a diazoamino moi
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