Herein we report the crystal structure geometry, optoelectronic and charge transport properties of (E)-1-(4-Bromophenyl)-3-(2-chlorophenyl)prop-2-en-1-one (1), (E)-3-(3-Bromophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (2) and (E)-3-(4-Chlorophenyl)-1-(2-furyl)prop-2-en-1-one (3) chalcone derivatives. In experimental part UV–vis-NIR, X-ray diffraction and Photoluminescence spectroscopy techniques were used. Additionally, quantum chemical density functional theory calculations were executed with a clear view to explore the linear optical, second and third-order nonlinear optical (NLO) properties as well as transfer integrals of all three systems. The experimental and theoretically calculated properties are found to be in excellent accord with each other. Comprehensible intra- and inter-molecular charge transport was observed from occupied to unoccupied molecular orbitals illuminating that these chalcones would be good choice to be used in various semiconductor devices. The compound (3) is found to have better NLO activities and thermal stability compared to (1) and (2). Larger electron transfer integral values than hole ones exposed that studied compounds would be better electron transport materials and can function as n-type in organic semiconductor devices.