Time-dependent density functional theory calculations are performed within a range-separated hybrid framework to quantify the efficiency of through-space charge transfer (CT) in organic rod-like push–pull compounds. Our model allows us to quantify the CT distance, the amount of transferred electron, as well as the spread of the charges. The impact of several kinds of variations has been investigated: (1) the nature and length of the π-conjugated bridge; (2) the strength of the terminal groups; (3) the presence of a central groups; and (4) the use of a polar environment. In α,ω-nitro-dimethylamino chains, we found that the charge transfer is maximized when four to six conjugated rings are separating the donor and the acceptor. The maximum CT distance is ca. 5 Å for these chains but can be improved by 1–2 Å in polar environments. Adding a stronger electron-donating group does not systematically induce an enhancement of the CT if a strong electron-accepting moiety is used, the latter tending to extract the electron from the conjugated chains rather from the donor moiety. There is indeed a fine equilibrium to respect to improve CT. This investigation is a further step toward the rational optimization of charge transfer properties.