Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes

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 BF2, as observed by 1H 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.

本文报道了一类含萘扎林（naphthazarin）的多环共轭烃的合成工作。研究以互变异构化的萘扎林核心骨架为底物，通过连续的狄尔斯-阿尔德（Diels–Alder）反应，构建得到目标共轭体系。通过与二氟化硼（BF2）络合，可实现分子骨架的完全共轭，该结果经核磁共振氢谱（1H NMR）与紫外-可见光谱（UV/vis spectroscopy）分析得以证实。此外，本研究还实现了对萘扎林醌类狄尔斯-阿尔德加合物10氧化程度的精准合成调控，并借此定向调控了其后续反应活性。最后，本研究验证了萘扎林作为结构基元，用于合成新型有机电子材料的应用潜力。