Display omitted •A systematic impact is studied by electron donating groups for chalcone derivatives.•A dual approach is used to study from molecule level to material level simulations.•Designed chalcones are found more suitable for electron transport than hole transport.•System 3 can transport charge about ~25 times higher as compared to systems 1 and 2.•A comparative analysis of electronic properties is also performed. In this study, three chalcone derivatives with a basic skeleton of 1,100-biphenyl-4-yl)-3-(3-nitrophenyl)prop-2-en-1-one are investigated. The basic skeleton was modified with the addition of three-terminal groups including hydrogen (1), methyl (2), and methoxy group (3). Using CASTEP Module, the optoelectronic properties are evaluated. The solid-state geometries of these systems are explored within the periodic boundary conditions (PBC). Among these systems, system 3 is found much better in terms of electron transport and optical properties such as dielectric function, absorption, conductivity, reflectivity, loss function, and refractive index. System 3 showed a higher dielectric function value about 3.7 at 1.8 eV thereby absorption 6.9 × 104 cm−1 at 300 nm and conductivity 1.2 fs−1 at 3.5 eV in the (001) plane. Furthermore, system 3 exhibited a high reflectivity and loss function in the (010) plane. Electronic band structure, the density of state, and electronic coupling analysis also reveal that system 3 has a potential application in charge transport devices. The study of electronic couplings that dominate the slowest electron hopping in a potential conductive path is roughly four to ten times larger for the holes than for the electrons. The transport pathways in systems 1 and 2 are 2D, while 1D in system 3. The bottleneck rate for electron transport is expected to be ~25 faster for system 3 than the other systems. This system 3 shows an excellent potential both at molecular and bulk levels for efficient charge transport material.