Schroeder Zachary W, LeDrew Joshua, Selmani Vanessa M, Maly Kenneth E
Department of Chemistry & Biochemistry, Wilfrid Laurier University Waterloo Ontario N2L 3C5 Canada
RSC Adv. 2021 Dec 13;11(62):39564-39569. doi: 10.1039/d1ra07931j. eCollection 2021 Dec 6.
Substituted triphenylenes show promise as organic semiconductors because of their ability to form columnar liquid crystalline phases featuring extended π-stacked arrays. While there are several methods for preparing triphenylenes, including oxidative cyclization reactions such as the Scholl reaction, as well as transition metal-catalyzed aryne cyclotrimerization, these methods are not effective for electron deficient triphenylenes. Here we demonstrate that the nickel-mediated Yamamoto coupling of -dibromoarenes is a concise and efficient way to prepare substituted triphenylenes, including electron-deficient systems that are otherwise challenging to prepare. We also demonstrate the application of this approach to prepare electron deficient discotic mesogens composed of triphenylenes bearing imide and thioimide groups.
取代苯并菲因其能够形成具有扩展π堆积阵列的柱状液晶相而有望成为有机半导体。虽然有几种制备苯并菲的方法，包括氧化环化反应如肖尔反应以及过渡金属催化的芳炔环三聚反应，但这些方法对缺电子苯并菲无效。在此，我们证明了镍介导的二溴芳烃的山本偶联反应是制备取代苯并菲的一种简洁有效的方法，包括那些否则难以制备的缺电子体系。我们还展示了这种方法在制备由带有酰亚胺和硫代酰亚胺基团的苯并菲组成的缺电子盘状液晶基元方面的应用。
