The binaphthyl metallocleft 2 in which an electrophilic uranyl cation is immobilized was synthesized by reaction of 1,2‐benzenediamine and aldehyde 5. According to 1H‐NMR spectroscopy, 2 is formed as a mixture of meso and racemic diastereomers (ratio 1:0.85). The complexation of 2 with pyridine, (iso)quinoline, acridine, benzylamine, and 1‐naphthalenemethanamine was investigated. The association constants of the complexes with aromatic amines vary from 3.5 · 102 to 3.6 · 106 M−1 (meso‐2) and 1.5 · 102 to 1.0 · 106 M−1 (racemic‐2). The higher stability of the complexes with meso‐2 is in agreement with the results of molecular mechanics calculations.