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A Supramolecular Protecting Group Strategy Introduced to the Organic Solid State: Enhanced Reactivity through Molecular Pedal Motion


  • We are grateful to the National Science Foundation (L. R. M., DMR-0801329) for funding.


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A supramolecular protecting group strategy has been applied to achieve solid-state photodimerizations of olefins lined with a combination of hydrogen-bond-donor and -acceptor groups. Esters were used as protecting groups to generate head-to-head photodimers that were readily converted into diacids. A protected olefin equipped with a stilbene unit exhibits enhanced reactivity that is ascribed to pedal motions in the solid state (orange hexagons: template: blur circles: recognition sites).