The synthesized perylene derivatives with an extended πsystem, incorporating a double bond and electron-withdrawing groups (EWG), exhibited a bathochromic shift of the dye towards the IR region. However, this modification significantly reduced their singlet oxygen generation capability. In contrast, introducing a triple bond led to a remarkably positive effect on these properties . Compounds 1, 2, and 4a-d, which retained high ΦΔ values and antiviral activity, appear to lack conjugation between the double bond and the perylene core. The introduction of EWGs into the perylene core shows potential for developing red-shifted perylene derivatives with improved solubility. Additionally, diversification of core dipole moments in perylene photosensitizers may enhance the design of antiviral compounds by enabling alternative affinity to viral envelopes and optimizing membrane localization. Nevertheless, further studies are needed to design a rigid core structure that maintains efficient ROS production while achieving these desirable characteristics.