Periphery Fusion Strategy of a Carbazole-Based Macrocycle toward Coplanar N-Heterocycloarene for High-Mobility Single-Crystal Transistors

Ning Zhang; Wenhao Li; Jiangyu ZhuTeng WangRong ZhangKai ChiYunqi LiuYan ZhaoXuefeng Lu

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Periphery Fusion Strategy of a Carbazole-Based Macrocycle toward Coplanar N-Heterocycloarene for High-Mobility Single-Crystal Transistors

机译：Periphery Fusion Strategy of a Carbazole-Based Macrocycle toward Coplanar N-Heterocycloarene for High-Mobility Single-Crystal Transistors

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Designing (hetero)cycloarenes through the modifications of the π-topologyand molecular packing of organic semiconductors has recently garneredconsiderable attention. However, their applications as an organic active layerin field-effect transistors are very limited, and the obtained hole carrier mobilitiesare less than 1 cm~2 V~(-1) s~(-1). In this work, a novel alkyl-substituted coplanarN-heterocycloarene (FM-C4) containing four carbazole units is successfullysynthesized in crystalline form. As compared to the corresponding singlebond-linked carbazole-based macrocycle M-C4, it is found that the peripheryfusion strategy greatly changes the electronic structures, energy levels, photophysicalproperties, host–guest interactions with fullerenes, and molecularcrystal stacking motifs. In particular, the fully fused N-heterocycloareneFM-C4 exhibits a herringbone packing structure with an unusual long-rangeπ?π overlap distance as low as 3.19 ?, whereas the single crystal of M-C4demonstrates no π?π interactions. As a consequence, FM-C4 in single-crystaltransistors displays the highest hole mobility of 2.06 cm~2 V~(-1) s~(-1), significantlyoutperforming M-C4 and all the reported (hetero)cycloarenes and suggestingthe high potential of (hetero)cycloarenes for organic electronic applications.

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来源
《Advanced Materials》 |2023年第20期|2300094.1-2300094.6|共6页
作者
Ning Zhang; Wenhao Li; Jiangyu ZhuTeng WangRong ZhangKai ChiYunqi LiuYan ZhaoXuefeng Lu;
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Department of Materials ScienceState Key Laboratory of Molecular Engineering of PolymersFudan UniversityShanghai 200438, P. R. China;

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(hetero)cycloarenes; conjugated macrocycles; high-mobility; periphery fusion strategy; single-crystal transistors;

Periphery Fusion Strategy of a Carbazole-Based Macrocycle toward Coplanar N-Heterocycloarene for High-Mobility Single-Crystal Transistors

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