Syntheses of N-[3,4,5-tris(n-dodecan-1-yloxy)phenyl] maleimide (6) and exo, exo-5,6-bis [[[3,4,5-tris(n-dodecan- 1-yloxy)benzoyl]oxy]methyl]-7-oxabicyclo[2.2.1]hept-2-ene (16) and their polymerization by radical, anionic and ring opening metathesis polymerizations, respectively, to yield the corresponding polymers 7 and 17 are described. Regardless of the polymerization method by which it was synthesized, 7 produced a hexagonal columnar (Phi(h)) liquid crystalline phase generated from the tubular architecture of the rigid 7/2 helical chain conformation surrounded by its tapered side groups. 17 also produces a Phi(h) phase. However, in this case, the assembly of tapered side groups of 17 into a tubular architecture induced a 3/1 helical chain conformation of its own flexible backbone. These two experiments support the model in which polymers containing tapered side groups form tubular supramolecular architectures by inducing a flexible helical chain conformation during the self-assembly of their own tapered side groups or by favoring the self-assembly of tapered side groups when a suitable rigid helical chain conformation is adopted by their own backbone.