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A synthetic strategy that produces previously rare unsymmetrical pentacene derivatives has been developed, broadening the chemical repertoire of this industrially useful class of compounds (Org. Lett., DOI: 10.1021/ol102349r). Pentacenes, a linear framework of five benzene rings, can be used to make a host of electronic materials, from organic semiconductors to solar cells. Until now, pentacenes have typically been symmetrical, and only rarely have examples with substituents in the pentacene framework’s 5-position been reported. Yoichiro Kuninobu, Kazuhiko Takai, and colleagues at Okayama University, in Japan, began by making unsymmetrical isobenzofurans via a rhenium-catalyzed C–H bond transformation from aromatic ketimines and aldehydes. They followed that step with a Diels-Alder reaction between the isobenzofurans and 1,4-anthraquinone. The reduced products yielded the unsymmetrical functionalized pentacenes. The team was able to attach alkoxy, trifluoromethyl, methoxycarbonyl, bromo, and thiophenyl functional groups to the 5-position. The researchers say that compared with other pentacenes these new derivatives are highly soluble in hexane, toluene, and tetrahydrofuran, which should ease processing in applications.
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