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Herein, we describe the synthesis, characterization and computational studies of novel 4-substituted phthalonitriles: (1) 4-(4-((benzothiazole)methyleneamino)phenoxy)phthalonitrile, (2) 4-(4-(3-phenylallylideneamino)phenoxy)phthalonitrile and (3) 4-(4-(4-isopropylbenzylideneamino)phenoxy)phthalonitrile. Compound 1 was obtained from the equimolar condensation reaction of 4-(4-aminophenoxy)phthalonitrile with benzothiazole-2-carboxaldehyde while compounds 2 and 3 were isolated from the reactions of 4-aminophenol with either cinnamaldehyde or cuminaldehyde followed by the nucleophilic substitution reactions of their respective Schiff bases and 4-nitrophthalonitrile. The spectral characterization of 1–3 was done using ¹H NMR, IR and UV–Vis spectroscopy, while structural confirmation could be affirmed from single TOF mass spectrometry and single crystal X-ray crystallography (for 1 and 2). Molecular …