The present study focuses on designing six new organic dyes derived from phenohydrazine, phenoxazine and phenothiazine, with modifications to the π-linker groups. Different characteristics, including structural, electronic, frontier molecular orbital, chemical reactivity, transition density matrix, molecule electrostatic potential, and driving force parameters, were examined using density functional theory (DFT) at the B3LYP/6–31 G (d,p) level. Additionally, the optical characteristics of the dyes in the CH2Cl2 solvent were evaluated using the time-dependent DFT (TD-DFT) with the TD-BH and H/6–31 G (d,p) method. Geometrical factors, optoelectronic qualities, frontier molecular orbitals, electrostatic surface potential, absorption spectra, and electron-accepting and -donating properties were all included in this thorough investigation. The examined dyes exhibited noteworthy properties, including λmax values ranging from 362.1 to 471.8 nm, band gaps within the range of 1.60–2.34 eV, a high LHE of approximately 0.994 for five dyes, indicating a robust electron-donating capacity, as well as a significant intramolecular charge transfer property. Notably, dyes featuring triazinyl outperformed those with phenyl among the designed compounds.