Heteroacenes, Novel Organic Semiconductors

计划合成较大的类癸烯分子（杂癸烯）。在杂苯中，一些芳香的C-H基团被吡啶型氮取代。研究小组将探讨氮环原子数量的增加对杂苯醚的光学、电化学和电学性质的影响。为了增加（提议的苯乙烯类型）的溶解度并加强芳香分子在固体状态下的相互重叠，他们将安装（三烷基硅基）乙基作为取代基。三烷基硅基有利于杂苯的固相处理。合成部分将扩展到卤化氮杂二烯，因为这些是目前非常感兴趣的电子传输材料，并且可以很容易地通过途中制备的中间体来制备。计划在固体载体上广泛研究杂间异构的薄膜形成。这些薄膜将通过显微镜和光谱学方法进行检查；研究小组计划通过有机配体来修饰下垫面的表面，以控制所提出的杂苯的堆叠和包装，以优化其与表面平行和垂直的电性能，并设想其在有机电子学中的潜在应用。所提出的异质化合物是用于n沟道薄膜晶体管的电子导电材料。杂苯应具有类似于并五苯（最重要的有机半导体）的电性能。它们可以传递电子而不是正电荷（空穴）。杂苯二烯可能允许构造具有反极性和反向电流的有机电子器件。这种反极性薄膜晶体管在先进的发光二极管和固态照明器件中作为驱动器具有广泛的重要性。PI已经建立了与少数民族高中合作的记录，并在HBCU （Clark Atlanta）教授高级有机化学课程。计划在本赠款期间继续进行这些活动。

The synthesis of larger acene-like molecules (heteroacenes) is planned. In the heteroacenes, some of the aromatic C-H groups are substituted by pyridine-type nitrogens. The groups will probe the influence of an increasing number of nitrogen ring atoms on the optical, electrochemical and electrical properties of the heteroacenes. To increase the solubility (of the proposed acene-types) and enforce mutual overlap of the aromatic molecules in the solid state,they will install (trialkylsilyl)ethynyl groups as substituents. The trialkylsilyl groups facilitate the solution-phase processing of the heteroacenes. The synthesis part will be expanded towards halogenated azapentacenes as these are of great current interest as electron transport materials and can be made readily by intermediates that are prepared en route. A broad investigation of the thin film formation of the heteroacenes on solid supports is planned. These thin films will be examined by microscopy and spectroscopic methods; the groups plan to modify the underlying surfaces by organic ligands to control the stacking and packing of the proposed heteroacenes to optimize their electric properties parallel and perpendicular to the surface and envision potential applications in organic electronics. The proposed heteroacenes are electron conducting materials for n-channel thin film transistors. The heteroacenes should have similar electric properties to pentacene (the most important organic semiconductor). They can transport electrons instead of positive charges (holes). Heteroacenes potentially allow the construction of organic electronic devices with reverse polarity and reverse flow of current. Such reversed-polarity thin film transistors are of broad importance as drivers in advanced light emitting diodes and solid-state lighting devices. The PI has established a track record for working with minority high schools and has taught an advanced organic chemistry class at an HBCU (Clark Atlanta). It is planned to continue these activities during this grant period.