Facile Synthesis of Bis‐pentafluoroarylated Anthracene Derivatives for N‐type Organic‐Field‐Effect Transistor Applications
Facile Synthesis of Bis‐pentafluoroarylated Anthracene Derivatives for N‐type Organic‐Field‐Effect Transistor Applications
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用于 N 型有机场效应晶体管应用的双五氟芳基化蒽衍生物的简便合成
DOI：
10.1002/chem.202203816
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Kuwabara Junpei
中科院分区：
文献类型：
--
作者：
Sato Ryota;Yasuda Takeshi;Hiroto Takanobu;Kanbara Takaki;Kuwabara Junpei
二苯蒽（DPA）及其衍生物是一种很有前途的p型有机场效应晶体管（OFFET）半导体材料。在这项研究中，为了开发具有蒽核的n型半导体材料，通过C-H直接芳基化将五氟苯引入蒽中，从而能够合成各种双（五氟苯基）蒽（DPA−F）衍生物。五氟苯C-H键的高反应性允许在一个步骤中直接芳基化合成DPA−F衍生物。强吸电子五氟苯基基团的引入为蒽衍生物提供了n型半导体性质，与母体DPA的p型性质相反。其中，2，6-二（五氟苯基）蒽具有较高的电子迁移率（0.12±0.02 cm 2/Vs），在OF 2 O3中的开/关比大于106。 高结晶度导致电子传输平稳。该研究为n型半导体材料提供了一种简便的合成方法，并为蒽上芳香取代基位置效应的分子设计提供了见解。
Diphenylanthracene (DPA) and its derivatives are promising semiconducting materials for p‐type organic‐field‐effect transistors (OFETs). In this study, to develop n‐type semiconducting materials with an anthracene core, pentafluorobenzene was introduced into anthracene by C−H direct arylation, enabling the synthesis of various bis(pentafluorophenyl)anthracene (DPA−F) derivatives. The high reactivity of the pentafluorobenzene C−H bond allows direct arylation for synthesizing DPA−F derivatives in a single step. The introduction of strong electron‐withdrawing pentafluorophenyl groups provides the anthracene derivatives with n‐type semiconducting properties, in contrast to the p‐type properties of the parent DPAs. Among the synthesized compounds, 2,6‐bis(pentafluorophenyl)anthracene shows a high electron mobility of 0.12±0.02 cm2/Vs and an on/off ratio>106in OFETs. The high crystallinity results in the smooth electron transport. This study provides a facile synthetic method for n‐type semiconducting materials and insights into the molecular design of the positional effects of aromatic substituents on anthracene.