Microwave synthesis, photophysical properties of novel fluorescent iminocoumarins and their application in textile printing

Abstract

Purpose -This paper aims to synthesise coumarine flourescent dyes from a cheap material in a very short time with a very high yield, and by using a clean green chemistry. Design/methodology/approach -Efficient microwave synthesis for some novel iminocoumarins starts from the reaction of p-phenyl-enediamine and ethyl cyanoacetate followed by cyclocondensation with salicylaldehyde derivatives. Findings -The synthesized iminocoumarine compounds were characterized by spectroscopic methods. Absorption and fluorescence spectra of the compounds were also recorded. All compounds were fluorescent in 1,4-dioxane solution, they all emitted blue light (440-460 nm). The printing properties were studied, and their applications on printing polyester and polyamide fabrics were studied by silk screen printing. Originality/value -The authors designed efficient microwavel synthesis for some novel iminocoumarine derivatives; The novel procedure features short-reaction time, moderate yields and simple workup; All compounds were fluorescent in 1,4-dioxane solution, and they all emitted blue light; The authors studied their application in printing polyester and polyamide fabrics.

Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

“…This is consistent with our recent observation that the desmethyl compound mentioned above is also formed as an unintended product by an exactly analogous reaction (Abdallah et al, 2022). The products thus represent, by coincidence, a continuation of our research on developing new benzothiazole and coumarin derivatives as organic fluorescent constituents (Elgemeie et al, 2015).…”

3-(Benzo[d]thiazol-2-yl)-2H-chromen-2-one

“…Molecules that incorporate benzothiazoles have attracted considerable research interest in the field of organic light-emitting diodes because of their unique electrooptical properties (Wang et al, 2010). Recently, we have synthesized some benzothiazoles data reports (Azzam et al, 2017a(Azzam et al, ,b, 2020a(Azzam et al, ,b,c, 2021Elgemeie et al, 2000a,b) and coumarin derivatives (Elgemeie, 1989;Elgemeie & Elghandour, 1990;Elgemeie et al, 2015).…”

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

“…Due to the great importance and application of this dye class, several green syntheses of this class of compounds have been explored (Safari and Zarnegar, 2015;Nikpassand and Pirdelzendeh, 2016;Nikpassand et al, 2018;Nikpassand, 2020). For instance, the microwave assisted threecomponent reaction of arylazopyrazoles, benzaldehydes and dimedone proceed via Mannich cyclization and condensation to form pyrazoloquinazolinone azo dyes 115 (Supplementary Material S42) (Elgemeie et al, 2015). The absorption maxima of azo dyes 115 appear between 380 and 498 nm.…”