There has always been interest in sterically hindered chromophores among the spectroscopist community,[1,2] and this study considers such interesting examples as derivatives of 2-(4-aminobenzylidene)-1,3-bis(dicyanomethylene)indane. Their UV-Vis absorption spectra comprises broad band in the red region, corresponding to two intramolecular CT transitions. Inequivalence of these is the direct consequence of steric hindrance between one of the dicyanomethylene groups and the aniline moiety. Interplay between tendency to form a planar, delocalized π-electron system and the other one, to reduce sterical hindrance, determines ground-state geometry with positive bond-length alternation (BLA) even in most polar solvents. The actual amount, as well as atomic charge sum on either the donor or the acceptor fragment, is considerably dependent on the density functional in use. Interestingly, when methyl subsituents on the aniline N atom are replaced with tritylacetoxyethyl ones, amount of charge transfer in the ground state mitigates significantly. In calculation of absorbance spectra, effects of different type of molecular cavity, iterative computation of the solvent reaction field and non-electrostatic interaction were also considered.