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The synthesis and structural analysis of a library containing 13 taper- and conical-shaped self-assembling dendrons, 16 dendritic monomers, and their corresponding polymers is reported. Fifteen of these polymers exhibit a well-defined cylindrical shape produced by the self-assembly of their dendritic side groups that self-organizes in a hexagonal columnar two-dimensional liquid crystalline lattice. The retrosynthetic analysis of this lattice by X-ray diffraction (XRD) showed that the diameter (60 to 41 Å) and the number of repeat units forming the cylinder cross-section (7 to 1.9) of these polymers are determined by the structure of their dendritic side groups. This demonstrates that, in the hexagonal columnar lattice, the conformation (from helical to fully extended) and the stiffness of the polymer backbone penetrating through the center of the cylinder are controlled in a systematic and predictive way by the structure of …