Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties

Abstract

In this study, the synthesis, characterization, and tautomeric properties of 2,2'-bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone, a new bisindandione derivative, were investigated. 2,2'-Bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone was obtained after the diazo coupling reactions between [5,5'-biindane]-1,1',3,3'-tetrone and aniline, and characterized by Fourier Transform-Infrared, proton nuclear magneticresonance, ultraviolet-visible and mass spectroscopy. The structural and spectroscopic analyses of azodye were examined using Density Function Theory, and vibration frequencies calculated with theoptimized structure were compared with experimental data. The obtained data showed that 2,2'-bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone could be found in two tautomers, and the molar ratio ofazo/hydrazo was found to be 0.86. The obtained data showed that the hydrazo form was dominant for2,2'-bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone.