By theoretically exploring the synergistic effects of electron donating (ED) and electron withdrawing (EW) substituents on intramolecular charge movement in disperse yellow (DY)119 dye, series of new azopyridone disperse dyes with improved aqueous solubility and chemical reactivity have been predicted using VWN-BP/DNP model. Aqueous solubility and reactivity of DY119 were found to be greatly dependent on the nature and position of substituent(s) on the primary DY119 structure. Momentous increase in solubility was observed with -CN and -NH2 substituents compared to other substituents. The new derivatives of DY119 showed appreciable thermodynamic stability. TiO2 and ZnO were predicted to be the most promising photocatalysts for the dyes. (C) 2018 Elsevier B.V. All rights reserved.