Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
J Org Chem. 2017 Jul 21;82(14):7470-7480. doi: 10.1021/acs.joc.7b01170. Epub 2017 Jul 3.
The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels-Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF, as observed by H NMR analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels-Alder adduct 10 is additionally demonstrated and enables us to direct its subsequent reactivity. Finally, this work serves to demonstrate the potential for naphthazarin as a building block in the synthesis of novel organic electronic materials.
本文描述了一组含萘并恶嗪的多环共轭烃的合成。在互变异构的萘并恶嗪核上进行顺序 Diels-Alder 反应，以获得最终的共轭体系。通过 1 H NMR 分析和紫外可见光谱观察到，通过与 BF 络合可以实现整个骨架的完全共轭。此外，还证明了对萘并恶嗪醌 Diels-Alder 加合物 10 的氧化程度进行精确的合成控制，并能够指导其后续反应性。最后，这项工作证明了萘并恶嗪作为合成新型有机电子材料的构建块的潜力。
