ORGN 306 |
Template-directed construction of molecular ladders in the solid state
| Tomislav Friscic, Xiuchun Gao, and Leonard MacGillivray. Department of Chemistry, University of Iowa, 305 Chemistry Building, Iowa City, IA 52242 |
| Synthetic approaches involving the ability to control molecular positioning are expected to promote the proficiency of chemists to synthesize complex molecules. Template-directed solid-state synthesis, a method being developed in our laboratory, utilizes linear template molecules to achieve such control in the solid state. Linear templates, specifically resorcinol derivatives, align olefins for a [2+2] photodimerization within discrete hydrogen-bonded assemblies. The modularity makes the method promising as a general way to conduct synthesis in the solid state. Consequently, using the method, we have synthesized a [2.2]-paracyclophane in quantitative yield. We now extend the scope of the approach to the construction of carbon-based molecular ladders. Using 5-methoxyresorcinol as the linear template, we have constructed, in the solid state, [3]- and [5]-ladderane frameworks, related to the ones recently discovered in lipid membranes of anammox bacteria in quantitative yields, starting from conjugated diene and triene reactants, respectively. 
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