A supramolecular protecting group strategy introduced to the organic solid state: Enhanced reactivity through molecular pedal motion

Abstract

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). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.