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首页> 外文期刊>Chemistry: A European journal >Exploration of the Photodegradation of Naphtho[2,3-g] quinoxalines and Pyrazino[2,3-b]phenazines
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Exploration of the Photodegradation of Naphtho[2,3-g] quinoxalines and Pyrazino[2,3-b]phenazines

机译：萘并[2,3-g]喹喔啉和吡嗪并[2,3-b]吩嗪的光降解研究

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摘要

Nitrogen-containing polycyclic aromatic hydrocarbons are very attractive compounds for organic electronics applications. Their low-lying LUMO energies points towards a potential use as n-type semiconductors. Furthermore, they are expected to be more stable under ambient conditions, which is very important for the formation of semiconducting films, where materials with high purity are needed. In this study, the syntheses of naphtho[2,3-g]quinoxalines and pyrazino[2,3-b]phenazines is presented by using reaction conditions, that provide the desired products in high yields, high purity and without time-consuming purification steps. The HOMO and LUMO energies of the compounds are investigated by cyclic voltammetry and UV/Vis spectroscopy and their dependency on the nitrogen content and the terminal substituents are examined. The photostability and the degradation pathways of the naphtho[2,3-g]quinoxalines and pyrazino[2,3-b]phenazines are explored by NMR spectroscopy of irradiated samples affirming the large influence of the nitrogen atoms in the acene core on the degradation process during the irradiation. Finally, by identifying the degradations products of 2,3-dimethylnaphtho[2,3-g]quinoxaline it is possible to track down the most reactive position in the compound and, by blocking this position with nitrogen, to strongly increase the photostability.
机译：含氮多环芳烃是有机电子应用中非常有吸引力的化合物。它们的LUMO能量较低，因此有可能用作n型半导体。此外，期望它们在环境条件下更稳定，这对于需要高纯度材料的半导体膜的形成非常重要。在这项研究中，萘并[2,3-g]喹喔啉和吡嗪并[2,3-b]吩嗪的合成反应条件可以提供所需的产物，高产率，高纯度且无需费时的纯化脚步。通过循环伏安法和UV / Vis光谱法研究了化合物的HOMO和LUMO能量，并研究了它们对氮含量和末端取代基的依赖性。核磁共振波谱分析了辐照样品中萘并[2,3-g]喹喔啉和吡嗪并[2,3-b]吩嗪的光稳定性和降解途径，证实并苯核心中氮原子对降解的影响很大。照射过程。最后，通过鉴定2,3-二甲基萘[2,3-g]喹喔啉的降解产物，可以追踪化合物中最活泼的位置，并通过用氮封闭该位置来显着提高光稳定性。

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