Comprehensive study of solvent effects on optical characteristics for novel pyrene-based chalcone compound: (E)-1-(benzo[d][1,3] dioxol-5-yl)-3-(pyren-1-yl)prop-2-en-1-one

Novel pyrene-based chalcone named (E)- 1-(benzo[d][1,3]dioxol-5-yl)- 3-(pyren-1-yl)prop-2-en-1-one (abbreviated as BDP) was synthesized to improve the application of chalcones in the manufacture of optical limiting devices. The molecular and optical properties of BDP pyrene-based chalcone were investigated experimentally and theoretically using FTIR, DFT, UV-Vis absorption, Z-scan, optical limiting (OL), and Photoluminescence (PL) for different solvents (toluene, dichloromethane (DCM), acetone, and dimethyl sulfoxide (DMSO)). The influence of solvation on the optical properties of the molecule was performed experimentally by UV-Vis absorption and theoretically using density functional theory (DFT) with the IEFPCM model at CAM-B3LYP exchange energy. The results show that the linear and nonlinear optical properties of BDP pyrene-based chalcone are highly dependent on solvent polarity. With the exception of toluene, the nonlinear refraction (NLR) character of the pyrene-based BDP chalcone increases with an increase in solvent polarity in the order of DCM> Acetone > DMSO, possibly due to strong delocalized pi-electrons, pi-pi interactions, and H-bonds in the chalcone compounds. In general, the BDP chalcone exhibited superior optical properties compared to DMDN, CPDAPP, and 2AT4C compounds as a result of the strong pi...pi interactions of pyrenyl chalcones as well as the longer conjugation span of BDP.