Polymer science in this century has focused on the linear chain and its derivatives such as star polymers, rings, combs, ladders, as well as nonlinear extensions such as branched polymers and three dimensional networks. This is a proposal to explore the conversion of molecules making up "bulk" polymers to two-dimensional forms analogous to sheets with thicknesses of "oligomeric" dimension. The principal investigators has already identified a possible synthetic pathway to achieve this goal but the methodology involves the use of fairly complex precursors. The work proposed here is aimed primarily at the synthetic simplification of pathways for two-dimensional polymers. Specifically it is proposed to follow several approaches with different levels of complexity. One approach involves the use of smectogens with biphenylic cores, and another the use of living polymerization to construct the necessary reactive oligomers. Other synthetic pathways are similar to those already developed in the principal investigator's laboratory using enantiomerically enriched chiral precursors. In the new approach, the requirement of enantiomeric purity is relaxed and substituted for the presence of several stereogenic centers. This is a Small Grant for Exploratory Research (SGER).