Large N-Heteroacenes

我们提出了大的N-杂并苯的合成和性能评价。将从几个方面加以说明。1)具有氯和氰基取代基的对称四氮杂并五苯作为薄膜晶体管电子传输材料的合成。2)结构多样性的扩展，氮杂并七烯和氮杂并八烯的合成，以及抑制还原和蝴蝶二聚化的发展策略，总是在较大的氮杂并苯中观察到。利用这种策略，我们将尝试制备氮杂并壬苯，但不清楚我们是否达到了稳定的极限，即使我们采用了空间和电子保护的组合。3)我们将制备三角氮杂并苯作为六氮杂环三萘（HATNA）类型的较大代表。4)我们将构建嵌入环丁二烯环的大氮杂并苯。我们的模块化方法允许使用市售或易于合成的试剂将构建块组合成新的分子拓扑结构。基础结构是我们的二乙炔化二氨基苯-萘和-蒽，它们与合适的二卤化物、邻醌或芳族邻二羟基化合物进行Pd催化偶联或经典缩合反应。第二部分研究了由此产生的氮杂并苯的材料性质。我们将以半系统的方式叙述氮杂并苯的分子结构、形貌和器件性能。这是可能的，因为我们已经建立了一个简单的设备制造和表征设施在海德堡。氮杂并苯是并五苯的近杂环亲戚，有助于这种方法。

We propose synthesis and property evaluation of large N-heteroacenes. Several aspects will be illuminated. 1) Synthesis of symmetrical tetraazapentacenes featuring chloro and cyano substituents as materials for electron transport in thin film transistors. 2) Extension of structural diversity, synthesis of azaheptacenes and azaoctacenes and developing strategies that suppress both reduction as well as butterfly dimerization always observed in the larger azaacenes. With this strategy we will attempt to prepare an azanonacene, but it is not clear if we do hit the limit of stabilization, even if we employ a combination of steric and electronic protection. 3) We will prepare triangular azaacenes as larger representatives of hexaazacyclotrinaphthylene (HATNA) types. 4) We will build up large azaacenes with embedded cyclobutadiene rings. Our modular approach allows the combination of building blocks into ever new molecular topologies employing commercially available or easily synthesized reagents. Basis structures are our diethynylated diaminobenzenes -naphthalenes and -anthracenes that undergo Pd-catalyzed coupling or classic condensation reactions with suitable dihalides, ortho-quinones or aromatic ortho-dihydroxy-compounds. The second part of the project investigates the materials properties of the thus produced azaacenes. We will relate molecular structure, morphology and device performance of the azaacenes in a semi-systematic way. This is possible as we have built up a simple device fabrication and characterization facility in Heidelberg. The azaacenes, close heterocyclic relatives of pentacene, lend themselves towards this approach.