The use of molecular photoswitches as possible agents in LAC approaches has been recently reported by different groups. In particular our groups have considered biomimetic analogues of cyclocurcumin (CC), a natural compound present in turmeric extracts together with the more common curcumin. Interestingly, both curcumin and CC may present antiparasitic and antibiotic activity and have been proposed in a PDT framework also for food decontamination. Both the natural CC and our derived chromophore possess an isomerizable double bond which can undergo E→Z isomerization. We have shown that, differently from the natural compound, our biomimetic analogous isomerizes under the effect of visible light independently of the solvent environment, and may interact with model lipid membranes. Furthermore, we have also confirmed, from an experimental and theoretical standpoint, that the isomerization is perturbing the membrane structural properties without its complete disruption. This property could then possibly trigger the apoptotic signal pathways, offering an original approach to LAC. In the present contribution we pursue the study of biomimetic analogs of cyclocurcumin (CC) involving different donor (hydroxy, ether, amine) and acceptor (oxo, malonitrile) groups, especially characterizing their optical, photophysical, and photochemical properties.