Triarylmethylium cations with the three rings linked by two bridging groups constitute a special class of [4]heterohelicenium dyes that combine high configurational stability with the optical properties of classic dye compounds. The racemization barriers and electronic circular dichroism of seven [4]heterohelicenium analogues are investigated with density functional theory to consider different design strategies. The racemization barriers are examined with the B3LYP functional utilizing the basis set 6-31+G* with respect to bridging heteroatoms in the helicenium motif and with different bulky substituents in the helix pitch. The racemization barriers of the [4]heterohelicenium are found to be highly dependent on the relative size of the bridging atom. Nucleophilic attack at the carbenium ion leads to formation of center adducts for which the racemization barriers are found to be lowered by 8-12 kJ/mol. This finding of a nucleophilic racemization catalysis may be rationalized by the loss of conjugation upon formation of an sp(3)-hybridized carbon in the center adducts. The effect of the heteroatom substitution and center adduct formation is reflected in the electronic properties of the compound calculated with the Coulomb-attenuated method CAM-B3LYP with the basis set 6-311++G**. The excitation energies are found to be highly dependent on the twisting of the helicenium framework and only weakly influenced by the electronic nature of the bridging substituent. The electronic circular dichroism is evaluated, as the rotational strength is found to be highly dependent on both the overall molecular structure and substitution pattern but with no simple correlation between structure and circular dichroism (CD) response. The calculations reveal that the magnitude of rotational strength in most cases is dominated by the angle between the electronic and magnetic transition dipole moments. Finally, it is found that computational screening of many different structures and substituents might be needed to find target structures with maximized rotational strength.