Photosensitized oxidation of alkenes with dendrimers as microreactors: controllable selectivity between energy and electron transfer pathway

Abstract

Carboxylic acid terminated poly(aryl ether) dendrimers were used as microreactors to conduct the photooxidation of trans-stilbene and trans,trans-1,4-diphenyl-1,3-butadiene (DPB) sensitized by 9,10-dicyanoanthracene (DCA) in aqueous media. The photooxidation pathways can be successfully controlled by encapsulating the substrate and sensitizer molecules in the same or different sets of dendrimers. The singlet oxygen can transfer from one dendrimer to another. After the photoreaction, products could be more easily extracted from a dendrimer than from a micelle or a vesicle, and the dendrimer can be simply recovered by neutralization of the solution and reused.