[structure: see text] Two-step syntheses of triple-bridged triscationic bicyclophanes are presented. Molecular modeling has been undertaken by means of ab initio calculations (6-31G level) on the triquinolina triscationic bicyclophane. This compound exists as two diastereomeric sets of enantiomers, one with C3 symmetry and the other with C1 symmetry. The C3-symmetrical derivative is 1.94 kcal mol(-1) more stable than its C1-symmetrical one. This energy difference is sufficient to consider the former and its enantiomer the only two conformations existing in solution at room temperature.