Darzi Evan R, Stanfield Dane A, McDermott Luca, Kelleghan Andrew V, Schwartz Benjamin J, Garg Neil K
Department of Chemistry and Biochemistry, University of California at Los Angeles Los Angeles California 90095 USA
Mater Adv. 2023 Jul 13;4(15):3351-3355. doi: 10.1039/d3ma00280b. eCollection 2023 Jul 31.
Polycyclic aromatic hydrocarbons (PAHs) are important compounds in materials chemistry, particularly for optoelectronic applications. One strategy for tuning PAH properties involves the net exchange of carbon atoms for heteroatoms, such as nitrogen. We report a comparative study of the well-known fluorophore 9,10-diphenylanthracene with an aza analog. The latter compound is accessed using a short sequence involving the use of two strained cyclic alkynes, benzyne and a 3,4-piperidyne, in Diels-Alder cycloaddition sequences. Comparative studies of 9,10-diphenylanthracene and the aza-analog show how the addition of a single nitrogen atom impacts electrochemical and optical properties. Organic light-emitting diode (OLED) devices were prepared using both compounds, which showed that nitrogen substitution leads to an unexpected red shift in electroluminescence, likely due to exciplex formation between the active layer and the 4,4'-,'-bis[-(1-naphthyl)--phenylamino]biphenyl (NPB) hole-transport layer. These studies highlight a unique approach to accessing heteroatom-containing PAHs, while underscoring the impact of heteroatoms on OLED device performance.
多环芳烃（PAHs）是材料化学中的重要化合物，尤其在光电应用方面。调节PAH性质的一种策略涉及碳原子与杂原子（如氮）的净交换。我们报道了对著名荧光团9,10 - 二苯基蒽与其氮杂类似物的比较研究。后一种化合物是通过一个短序列获得的，该序列涉及在狄尔斯 - 阿尔德环加成序列中使用两种张力环状炔烃，即苯炔和3,4 - 哌啶炔。9,10 - 二苯基蒽和氮杂类似物的比较研究表明，单个氮原子的加入如何影响电化学和光学性质。使用这两种化合物制备了有机发光二极管（OLED）器件，结果表明氮取代导致电致发光出现意外的红移，这可能是由于活性层与4,4'-，'-双[ - （1 - 萘基） - - 苯基氨基]联苯（NPB）空穴传输层之间形成了激基复合物。这些研究突出了一种获取含杂原子PAHs的独特方法，同时强调了杂原子对OLED器件性能的影响。
