New tricyanofuran intramolecular charge transfer dyes comprising the hydrazone group were prepared and fully characterized in order to study their possible solvatochromism, dyeing ability, and antimicrobial activity. e preparation of the hydrazone dyes was achieved in relatively good yields starting from different aromatic amines. e hydrazone functional group was presented via the azo-coupling reaction of the tricyanofuran compound by the properly substituted diazonium chloride. Chemical structures of the prepared hydrazones were confirmed via nuclear magnetic resonance spectroscopy ( 1 H-and 13 C-NMR), Fourier-transform infrared spectroscopy (FT-IR), and elemental analysis (C, H, and N). e UV-visible absorption spectra of the produced sensor colorants displayed interesting solvatochromism in solvents with a different polarity, which was found to be affected by the substituents bonded to the aromatic hydrazone moiety. e pH molecular switching was investigated through tuning the intramolecular charge transfer stimulated by the reversible deprotonation/protonation process in acetonitrile solution showing color change from yellow to purple. e produced disperse dyestuffs were employed for dyeing polyester fibers to introduce acceptable color strength and colorfastness properties. Moreover, the dyes verified a weak to moderate antimicrobial activity against some selected pathogens, including S. aureus, E. coli, and Candida albicans.