Modular Synthesis of Imidazolyliden-substituted chinoid Heteroacenes

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In recent years, organic semi conductors emerged from the academic level to industrial applications e.g. in OLEDs, OFETs or organic solar cells. Despite these achievements the demand for material and novel structures is unbroken. This clearly requires the development of novel and modular synthetic approaches to access new structures or to produce the desired amount of material. The project aims at the efficient synthesis of a series of novel quinoid imidazolylidene heteroacenes through the palladium-catalyzed carbon-sulfur or carbon-nitrogen cross coupling and simultaneous cyclization to access sulfur- or nitrogen-containing heterocycles respectively.This modular synthetic approach through catalytic methods allows for the easy modification of the central as well as the peripheral groups, so that a library of these new compounds is readily available. These structures will be investigated as ambipolar semi conductors in OFETs and as novel donor and acceptor materials in organic solar cells. Furthermore, this synthetic approach does not only pave the way to novel quinoid structures but simultaneously provides a new general synthetic access to heteroacenes.