Molecular crystals provide fertile ground to explore the recognition profile of organic frameworks and functional groups. Since the application of such studies hold much importance to a wide variety of materials, it is not surprising that recent efforts have developed new strategies for constructing ordered supramolecular architectures. Chemical transformations conducted in the solid-state provide one area that has received focused attention. Advances in this area over the last decade delivered innovative structural tools for controlling the spatial orientation of reacting species. Our interest with solid-state reactivity has centered on rationally designed aryl sulfonamides that organize in the solid-state by use of the complementary features of molecular topology and non-bonded contacts. These materials form robust supramolecular dimers that undergo chemo- and enantioselective [2+2] photodimerizations. Since many of these systems proceed by quantitative single-crystal-to-single-crystal transformations, crystallographic investigation of the reactant and product phases offers key insight to the structural features responsible for these highly-selective processes. This presentation will discuss the design and operational aspects of engineered molecular assemblies that result in entantiocontrolled reaction outcomes, future directions, and the role of student researchers at a PUI to program success.

New frontiers in desymmetrized molecular crystal reactions

246th National Meeting (2013)

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