Fabrication of photoluminescent nanoparticles from carbazole-derived chalcones: a study of optical properties, cell biomarking, and metabolism

Abstract

In this work, the synthesis by Claisen–Schmidt condensation of two new chalcones: (2E)-3-[4-(9H-carbazol-9-yl)phenyl]-1-(2,4-difluorophenyl)prop-2-en-1-one (M1) and (2E)-3-[4-(9H-carbazol-9-yl)phenyl]-1-(3,4-difluorophenyl)prop-2-en-1-one (M2), with a donor–acceptor structure for photonic applications is reported. The characterization of the optoelectronic properties is evaluated, the two chalcones have photoluminescence in both solution and in the solid state, however, the intensity of the photoluminescence is higher in the solid state (I/I₀ = 2). The electronic distribution of M1 and M2 was studied by the solvatocromismo and acidochromism experiment, where it was determined that the absorption and emission of the molecule change according to the polarity of the solvent. The D–A structure was corroborated by the data obtained by DFT analysis using the B3LYP functional and the 6-31G(d) base. Silica precursor-coated nanoparticles were fabricated by the microemulsion method, obtaining spherical biocompatible nanoparticles with a size distribution of 42 nm and Φ_F of 8% and 18% for M1 and M2 respectively. Cytotoxicity tests were carried out on different cell lines, healthy cells, colon cancer cells, and breast cancer cells, finding that the NPs coated with silica were not cytotoxic, but when irradiated at 366 nm for 1 h, the population of diseased cells is reduced almost entirely.