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The rational design, the synthesis via a new convergent approach, and the characterization of four generations of monodendrons based on the AB₃ building block methyl 3,4,5-trishydroxybenzoate are described. The first generation monodendrons are crystalline. The second generation methyl 3,4,5-tris-3‘,4‘,5‘-[tris(n-dodecyloxy)benzyloxy]benzoate (12Gn-AG-CH₃, n = 2), the corresponding benzyl alcohol (12G2-AG-CH₂OH) and benzoic acid (12G2-AG), and all higher generation monodendrons with n = 3 and 4 exhibit in addition to the crystal phase an isomorphous cubic liquid-crystalline (LC) phase of Pm3̄n space group. The cubic unit cell parameters of 12G2-AG, 12G3-AG, and 12G4-AG are 68.3, 79.2, and 84.0 Å, respectively. Computed electron density profiles demonstrated that in the cubic phase 12, 6, and 2 monodendrons of generation 2, 3 and 4 are self-assembled in supramolecular dendrimers …