Three new squaraine-based functional π-conjugated molecules were synthesized considering the core and wings concept. The molecules, , , and , were end-capped with three different wings, such as malononitrile, 2-(3-hexyl-4-oxothiazolidin-2-ylidene)malononitrile, and 3-ethyl-2-thioxothiazolidin-4-one. Among the three dyes, showed the highest molar extinction coefficient. The photoluminescence of all the dyes showed an opposite trend to that of the absorption maximum. The electrochemical results showed that the lowest unoccupied molecular orbital level of all the dyes ranged from -3.72 to -3.82 eV, whereas the highest occupied molecular orbital ranged from -4.89 to -4.94 eV. Solvatochromism was carried out to observe the effects of the solvent containing the dyes. The electronic structure of the dyes was examined using simulations. The dyes were characterized theoretically, and the red-shifted absorption of was explained and correlated with its biradicaloid character and singlet-triplet energy gap.