Modular Synthesis of Imidazolyliden-substituted chinoid Heteroacenes

近年来，有机半导体从学术水平发展到工业应用，例如在有机发光二极管、场效应管或有机太阳能电池中的应用。尽管取得了这些成就，但对材料和新颖结构的需求从未中断。这显然需要开发新颖和模块化的合成方法来获得新的结构或生产所需数量的材料。该项目旨在通过钯催化的碳-硫或碳-氮交叉偶联和同时环合来分别获得含硫或含氮的杂环，从而有效地合成一系列新型的喹啉咪唑亚甲基杂苯。这种通过催化方法实现的模块化合成方法允许中心基团和外围基团易于修饰，因此这些新化合物的文库很容易获得。这些结构将作为场效应管中的双极半导体和有机太阳能电池中的新型施主和受主材料进行研究。此外，这种合成方法不仅为新的奎宁结构铺平了道路，同时也提供了一种新的合成杂环苯的途径。

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.