The preparation and characterization of a series of first to fourth generation dendronized poly-(norbornene)s are presented. The monomers were synthesized in a divergent fashion from 5-norbornene-2-methanol, utilizing the acetonide protected anhydride of 2,2-bis(methylol)propionic acid. The norbornenyl bearing dendrons were polymerized by ring-opening metathesis polymerization, and it was found that the Grubbs' first generation catalyst resulted in polymers with lower polydispersity compared to the materials obtained when employing the second generation catalyst. Two series of first to fourth generation polymers were characterized by DSC, SEC, and dynamic rheological measurements. In addition, it was found that the fourth generation material could form regular, porous membranes and birefringent fibers. The membranes were characterized with atomic force and optical microscopy. The birefringent fibers were analyzed with X-ray diffraction, polarized FTIR, and polarized optical microscopy.