In organic chemistry, aromaticity is a fundamental concept. The aromaticity of traditional aromatic compounds usually comes from the high delocalization of π-electrons on the upper and lower planes of the ring, while σ-aromaticity mainly comes from the intramolecular σ bond and orbital overlap, both of which can affect the electron transport capacity of the molecule. In this study, density functional theory combined with non-equilibrium Green's function (DFT＋NEGF) method are used to systematically investigate the aromaticity and electronic transport properties of benzene, thiophene, furan, and their derivatives. The computational results reveal that both π-aromaticity and σ-aromaticity have pronounced effects on molecular electronic transport, where σ-aromaticity shows a positive correlation with electron transmission, whereas π-aromaticity displays a negative correlation. The charge transfer properties of diphenyl dithiol (DB), dithiophene dithiol (DT) and difuran dithiol (DF) molecules containing two aromatic rings are significantly influenced by molecular planarization. Moreover, the furan ring in DF exhibits a larger NICS(1)_zz value than the thiophene ring in DT. Furthermore, aromatic compounds typically exhibit a better coplanar trend. The molecular design strategy involving the modification of DT and DF molecules with F atom generates intramolecular F…S and F…O non-covalent interactions, which significantly enhance molecular planarity and rigidity. Meanwhile, the virtual five-membered ring structures containing intramolecular F…S and F…O interactions have σ-aromaticity characteristics, effectively promoting electron transport along F…S and F…O pathways, thereby improving the electron transport capacity. This research contributes to further understanding of the intrinsic relationship between molecular aromaticity and electronic transport capacity, and provides strategies for designing more efficient electronic devices in the future.