We have synthesized and characterized 4,4’-bis(4-0-methacrylstryl)-2,2’-bipyridine which forms stable, transferable Langmuir-Schaefer films at the air-water interface. The Langmuir film shows a liquid-solid phase transition with the respective extrapolated areas of 43 and 32 Angstrom(2)/molecule. These films were transferred to quartz, Au, and Ge substrates with transfer ratios of 1.0 +/- 0.1. Characterization of the resulting multilayer films show that films transferred before the phase transition give relatively isotropic films and strongly anisotropic films from transfer after the phase transition. We have polymerized this material in CHCl3 solutions using both Co-60 gamma-rays and AIBN, a radical source, and characterized the resulting materials. We have also polymerized Langmuir-Schaefer multilayers using gamma-rays. Under the conditions used, gamma-irradiation only polymerizes oriented films, leaving isotropic films intact. Radical polymerization of aggregated solutions leads to aggregated polymeric material where gamma-irradiation of solutions leads to unaggregated polymeric chains. We conclude that there is a topochemical requirement for polymerization to occur in the 2-D solid state and preorganization before polymerization in solution can lead to new materials.