9,10-Dichlorooctafluoroanthracene (1) was synthesized from commercially available tetrafluorophthalic acid by an optimized solution-phase route. To establish 1 as a synthon for n-type organic semiconductors, the compound was reacted with phenylboronic acid under modified Suzuki−Miyaura coupling conditions to generate octafluoro-9,10-diphenylanthracene (7) in high yield. Cyclic voltammetry and X-ray crystallography indicate that 7 has a stabilized LUMO energy level and exhibits extended π stacking, which should lead to efficient electron transport in solid-state devices. 1,2,3,4,5,6,7,8-Octafluoroanthracene (2) was also synthesized as a potential n-type building block, but suitable C−C coupling conditions for this compound were not found, and 2 could not be converted into 9,10-dibromooctafluoroanthracene or octafluoro-9,10-diiodoanthracene.

中文翻译：

---

9,10-二氯八氟蒽作为n型有机半导体的基础材料

通过优化的溶液相路线，由市售的四氟邻苯二甲酸合成9,10-二氯八氟蒽（1）。为了建立1作为n型有机半导体的合成子，在改良的Suzuki-Miyaura偶联条件下，使该化合物与苯基硼酸反应，以高收率生成八氟-9,10-二苯基蒽（7）。循环伏安法和X射线晶体学分析表明7具有稳定的LUMO能级并表现出扩展的π堆积，这应该导致固态器件中的有效电子传输。1,2,3,4,5,6,7,8-八氟蒽（2）也被合成为潜在的n型结构单元，但没有找到适合该化合物的C-C偶联条件，并且2无法转化为9,10-二溴八氟蒽或八氟-9,10-二碘蒽。