We have reported here the complexation and chiroptical behavior of the host-guest complexes using a new chiral Zn(II) bisporphyrin tweezer host and a series of achiral aliphatic diamine guests varying the chain length. (1R,2R)-Cyclohexanediamine covalently links two Zn(II) porphyrin moieties, which thereby produces a strong chiral field around the bisporphyrin tweezer framework. The chiral tweezer upon complexation with achiral guest exhibited large changes in the UV-vis spectra and CD exciton couplets due to a sudden change in the porphyrin disposition, which is controlled by the host-guest stoichiometry as well as the chain lengths of the diamine guest. Addition of smaller diamines (n: 2-5) to the host resulted in the formation of 1:1 sandwich and 1:2 open complexes, respectively, at the low and high guest concentration, which eventually display two-step inversions of the CD couplet. With longer diamines (n: 6-8), however, only 1:1 sandwich complexes are formed with retention of the CD sign. Similar observations were also reported by us recently using another chiral bisporphyrin tweezer having (1R,2R)-diphenylethylenediamine as the spacer. In an effort to obtain deeper insights into the sudden changes of interporphyrin disposition just by changing the length of the achiral diamines, we have extended a series of computational studies and correlated closely with the results obtained from the experiment. While the previously published study has relied on commonly applied Monte Carlo (MC) sampling of the potential energy surface in addition to being guided by porphyrin effective transition moment approximation, the present study uses a considerably more robust molecular modeling protocol, namely Molecular Dynamics (MD) simulations followed by full ab initio geometry optimization and TD-DFT CD prediction. The experimental data corroborate with the results obtained from the theoretical conformational analysis. The latter are also supported by experimental 1 H NMR data empowered by the porphyrin ring-current effect. The NMR spectral patterns of pyrrolic protons of the free host and the 1:1 sandwich complexes appear very diagnostic and reflect the changes in the mutual porphyrin disposition on moving from the free host to the complexed ones with short and long diamines. Overall, the experimental NMR data underscore the sensitivity of pyrrolic protons chemical shifts to subtle alterations of the geometrical features, and as such, they come in agreement with the theoretically derived models.