Supramolecular Systems as Microreactors:  Control of Product Selectivity in Organic Phototransformation

• Published in: Accounts of chemical research Vol. 36; no. 1; pp. 39 - 47
• Main Authors: Tung, Chen-Ho, Wu, Li-Zhu, Zhang, Li-Ping, Chen, Bin
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.01.2003
• ISSN: 0001-4842; 1520-4898
• DOI: 10.1021/ar010141l

This Account reviews the developments in microreactor-controlled selectivity in organic phototransformation. Photocycloaddition of α,ω-diaryl compounds with long flexible chains within Y-type zeolite and low-density polyethylene films leads to formation of intramolecular cyclomers to the exclusion of intermolecular products. ZSM-5 zeolite, Nafion membranes, and vesicles as hosts direct photosensitized oxidation of alkenes selectively toward either the energy-transfer-mediated or the electron-transfer-mediated products. Zeolites, Nafion membranes, and microemulsions as microreactors remarkably control chemo-, regio-, and stereoselectivity in the photochemical reaction of phenyl phenylacetates, photocycloaddition of anthracenes, and photocyclization of azobenzene and stilbazole.