Design and Synthesis of Difluoroboronite Curcuminoid derivatives for application in photodynamic therapy

This research paper describes the synthesis of two derivatives, 1 and 2, using aldehydes containing acid-sensitive groups. Both derivatives are of the donor-acceptor-donor type and exhibit absorption and emission in the red region. Derivative 1 has an absorption peak at 647 nm and an emission peak at approximately 713 nm. These molecules possess intramolecular charge transfer properties, allowing them to populate a triplet state that produces singlet oxygen, which plays a crucial role in cell death. Furthermore, the acid-sensitive groups on these derivatives enable selective accumulation in slightly acidic cancer cells. The cellular uptake of these derivatives can be enhanced through the formation of nanoaggregates, with average particle sizes of 112 nm and 81 nm for 1 and 2, respectively. While derivative 2 has a higher capacity for singlet oxygen production (φΔ∼0.40) and better fluorescence quantum yield than derivative 1, both molecules have high molar absorption coefficients and can serve as potential photosensitizers for cancer treatment.