Dyeing performance on polyester fibers and DFT investigation of newly synthesized 2-arylazo-dioxoisoindolinecyanoacetamide derivatives

Abstract

A series of aryl-diazinyl-cyanoacetamide (<b>2a–l</b>) were prepared by coupling the appropriate diazotized arylamines with dioxoisoindoline cyanaoacetamide (<b>1</b>). Also, the cyclization of azo derivatives (<b>2f</b>, <b>2h</b>, and <b>2j</b>) with chloroacetonitrile to yield the pyrazole derivatives (<b>5f</b>, <b>5h</b>, and <b>5j</b>) was studied. Moreover, compound <b>2d</b> reacts with malononitrile to afford compound (<b>6e</b>). In a similar manner compound, <b>2d</b> reacts with hydroxylamine to afford the sole product tetrazine derivative <b>8d</b>. All the newly synthesized compounds were fully characterized by both analytical and spectral analyses. The geometries of the azo and hydrazo tautomeric forms were optimized at the <b>B3LYP/6-311G</b> level of theory. The dyeing performance of the synthesized dyes on polyester fibers has been assessed. Most of the dyes showed a good affinity to polyester fibers. No details regarding the synthesis and dyeing performance of such dyes are reported before in the literature.