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Excellentπ-bowl Semiconductors Based on C_(70)Subunit

CCS Chemistry 2024年第2期6卷 353-364页

作者： Meng Chen Yuxiao Duan Xinyue Liu Qian Zhan Hironobu Hayashi Kyohei Matsuo Hiroko Yamada Guangpeng Gao Yonghao Zheng Lei Zhang Beijing Advanced Innovation Center for Soft Matter Science and Engineering Beijing University of Chemical TechnologyBeijing 100029 School of Optoelectronic Science and Engineering University of Electronic Science and Technology of China(UESTC)Chengdu 610054 Division of Materials Science Nara Institute of Science and Technology(NAIST)IkomaNara 630-0192 Key Laboratory of Cluster Science of Ministry of Education Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion MaterialsSchool of Chemistry and Chemical EngineeringBeijing Institute of TechnologyBeijing 100081

As open substructures of fullerenes,aromaticπ-bowls are promising candidates as new organic semiconductors,as well as attractive hosts for *** demonstrate herein the synthesis and characterization of a novel C_(2v)symmetricπ-bowl,pyracyleno[6,5,4,3,2,1-pqrstuv]pentaphene(3).bowl 3 was equipped with two distinctive reactive sites,allowing for bromination and cross-coupling reactions to readily yield functionalized bowls with two 2,4,6-trimethylphenyl(5)and triethylsilyl(TES)-ethynyl(6)substituents,***-temperature 1H NMR analysis and density functional theory(DFT)calculations indicated bowl-to-bowl inversions of 3,5,and 6 at room *** alternating the substituents,the crystal structures of the threeπ-bowls 3,5,and 6 could be controlled from 1D linear to 1D slipped to 2D herringbone packing motifs,providing insight into the packing behavior ofπ-bowls.1H NMR titration study indicated that the TES-ethynyl substituent enhanced the ability ofπ-bowl to bind C_(70)with an association constant of 2485 M−*** C_(70)molecules withπ-bowls 3 and 6 formed 1:1 complexes,in which C_(70)molecules aggregated into zig-zag and 1D linear arrays,*** hole mobility of 2.3 cm^(2)V^(−1)^s(−1)and electron mobility of 0.16 cm^(2)V^(−1)^s(−1)ofπ-bowl 3 and its complex with C_(70)were demonstrated,respectively,which proved a great value for the development of aromaticπ-bowl semiconductors with tunable properties for organic electronic devices.

关键词： organic semiconductor π-bowl fullerene crystal engineering mobility

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