Synthesis and Solvatochromic Properties of Novel Azo-azomethine Dyes

Abstract

Dyes bearing imino group along with azo one in the structure, present the class of azo-azomethine dyes. Azomethine compounds, known as Schiff bases, find application in biomedical research considering their potential antibacterial, antifungal, antimalaric, anticancer, antiinflammatory and antiviral activity. Furthermore, azo dyes are used in textile fiber dyeing, ink-jet and laser printers, LCDs, photovoltaic devices and metal complexes. With respects to the strong biological activity and a broad spectrum of potential application in industry, herein the microwave assisted synthesis and characterization of three new azo-azomethine dyes is presented. New azo-azomethine dyes were obtained by merging arylazo pyridone dye with different aniline cores resulting in azo-azomethine structure. In addition, tautomerism and solvatochromic properties of the dyes have been discussed.

Organske sintetske boje koje u svojoj strukturi sadrže azo i imino grupu predstavljaju klasu azo-azometinskih jedinjenja. Azometinska jedinjenja, poznata kao Schiff-ove baze, imaju značajnu ulogu u biomedicinskim istraživanjima zbog potencijalne antibakterijske, antifungalne, antimalarijske, antikancerogene, antiinflamatorne i antivirusne aktivnosti. Azo-azometinske boje se mogu koristiti u industriji za bojenje tekstilnih vlakana, zatim u LCD ekranima, ink-džet i laserskim štampačima, fotonaponskim uređajima i metalnim kompleksima. U ovom radu prikazana je mikrotalasna sinteza i strukturna karakterizacija tri nove azo-azometinske boje, polazeći iz arilazo piridonske boje i različito supstituisanih anilina. Solvatohromna svojstva i tautomerija novih azo-azometinskih jedinjenja proučavani su u rastvaračima različitih svojstava.