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Large N-Heteroacenes: New Tricks for Very Old Dogs?



Azaacenes have been known for a very long time, either as N,N′-dihydro compounds or in their oxidized form as 4 n+2π systems, but only recently have processable and charcterizable derivatives been sought. In the last three years synthetic routes to large N-heteroacenes have been developed. In particular, the Pd-catalyzed coupling of aromatic diamines with activated aromatic dihalogenides has enabled simple access to numerous new azaacenes. Since 2010, azapentacene and stabile oligoazahexacene have been synthesized, as well as a symmetrical tetraazapentacene, which acts as an excellent electron-transport material for thin-film transistors.

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