We systematically designed and developed three novel halogenated aza-octacene derivatives, which have the same π-conjugated backbone with different terminal halogen groups (F, Cl, Br). These aza-octacene derivatives are synthesized by acid-catalyzed condensation of naphthalene-bisisatin with 4,5-dihalo-1,2-phenylenediamine. The in-depth experimental and theoretical analyses on these molecules, using the non-halogenated system as a reference, allowed us to understand the impact of halogenation on electronic and optical properties. Both electronic affinity (EA) and ionization potential (IP) are increased through peripheral halogen substitution. Chlorination enhances the EA more effectively compared with fluorination and bromination. Micro-crystal devices based on the bromine substituted aza-octacene derivative show only p-type charge transport behavior. In contrast, the chlorinated and the fluorinated aza-octacene derivatives exhibit ambipolar charge transport.

我们系统地设计和开发了三种新颖的卤代氮杂辛烯衍生物，它们具有相同的π共轭主链，具有不同的末端卤素基团（F，Cl，Br）。这些氮杂八碳烯衍生物是通过萘-双isatin与4,5-二卤代1,2-苯二胺的酸催化缩合反应合成的。使用非卤代系统作为参考，对这些分子进行了深入的实验和理论分析，使我们能够了解卤代对电子和光学性质的影响。电子亲和力（EA）和电离电势（IP）都通过外围卤素取代而增加。与氟化和溴化相比，氯化更有效地增强了EA。基于溴取代的氮杂-并八苯衍生物的微晶器件仅显示p型电荷传输行为。相反，氯化的和氟化的氮杂辛并苯衍生物表现出双极性电荷传输。