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Stratingh lecture - Sara Eisler: Synthesis, Cyclizations and Switches: Controlling Regiochemistry and Molecular Motion in π-Extended Heterocycles

Wanneer:vr 22-04-2016 13:00 - 14:00

We have found that intramolecular, nucleophilic cyclization reactions can be per-formed under mild conditions to give a variety of p-extended isoindolinone (IIN), pyrrolone, and pyridinone containing products in high yields. Multiple cyclizations can be performed simultaneously within a single molecule, and these extended sys-tems are thermally stable, easily functionalizable, and strongly fluorescent. In ad-dition, controlled switching between isomeric forms of the IINs can be induced when exposed to UV and visible light, thus representing an entirely new family of multi-stable molecular switches. We have used the sequential E-Z isomerizations of photoresponsive IIN moieties to build multi-stable molecular switches with unusual switching motifs. These systems can be reversibly and controllably trans-formed between several different stable conformations, and will respond to or-thogonal stimuli. The synthesis, electronic properties, and switching characteristics of several responsive IIN-containing small molecules will be presented