Chiroptical sensing based on circular dichroism (CD) or circularly polarized luminescence (CPL) enables analyses with greater sensitivity and resolution than traditional methods. However, there is not any extensive collection of chromophoric platforms for the synthetic development of chiroptical sensors, their research arousing great interest in recent years. In this sense, synthetically-accessible and conformationally flexible chiral bis(BODIPYs) based on enantiopure C₂-symmetric diamines or diols (helicoBODIPYs) have demonstrated to have appealing chiroptical properties, which significantly depend on the dye preferred helical geometry in solution. Therefore, they could be used as chromophoric platforms for the development of accessible (low cost) chiroptical sensors. In this context, easy at-bridge functionalization in helicoBODIPYs could be used to rapidly develop reactive scaffolds towards sensors. However, knowledge about the influence of this functionalization on the photophysics and chiroptics of the helicoBODIPY is required first. To this end, this communication describes preliminary results concerning the unexpected influence of the at-bridge electronic factors on the photophysics of helicoBODIPYs, mainly due to changes in the probability of undergoing photoinduced intramolecular charge transfer (ICT) processes. These results cast light on the key factors controlling the design of helicoBODIPYs as chiroptical sensors, showing that not only changes in the at-bridge steric factors affect the signalling (e.g., by means of changes in the dye helical geometry by an external stimulus), but also changes in the at-bridge electronic factors.