Covalent capture of supramolecular architecture in the solid state using linear templates

ORGN 307

Leonard R. MacGillivray, Giannis S. Papaefstathiou, Tomislav Friscic, Tamara D. Hamilton, and Dushyant B. Varshney. Department of Chemistry, University of Iowa, Iowa City, IA 52242
Tools that pick individual atoms and molecules from the environment and place them in position for reaction are anticipated to have widespread applications in chemical synthesis and materials science (e.g. molecular nanotechnology). In this context, we are developing an approach that permits ditopic molecules (e.g. resorcinol), which function as linear templates, to position complementary olefins (e.g. bis(pyridyl)ethylenes) within supramolecular architectures in the solid state for chemical reaction to form covalent bonds. The templates operate by preorganizing reactants via hydrogen bonds for single and multiple [2+2] photodimerizations. In this presentation, we will demonstrate how linear templates enable chemists to covalently construct molecular targets. The targets include linear and bent molecules, as well as molecular ladders. The targets form in the solvent-free environment in 100% yield and in gram quantities.
 

Molecular Recognition and Materials
8:00 AM-12:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- 201B, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004