Herein, we describe the design, synthesis, structure, and function of synthetic, supramolecular ß-barrel models. Assembly of octi(p-phenylene)s with complementary -Lys-Leu-Lys-NH2 and -Glu-Leu-Glu-NH2 side chains yielded water-soluble rigid-rod ß-barrels of precise length and with flexible diameter. A hydrophobic interior was evidenced by guest encapsulation. Host-guest complexes with planarized, monomeric ß-carotene within tetrameric rigid-rod ß-barrels, and disc micellar astaxanthin J-aggregates surrounded by about dodecameric rigid-rod bicycle tires were prepared from mixed micelles by dialytic detergent removal. The significance of these findings for future bioorganic chemistry in confined, intratoroidal space is discussed in comparison with pertinent biological examples.