Rational Functionalization of a C70 Buckybowl to Enable a C70:Buckybowl Co-crystal for Organic Semiconductor Applications,Journal of the American Chemical Society

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Rational Functionalization of a C70 Buckybowl to Enable a C70:Buckybowl Co-crystal for Organic Semiconductor Applications
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-01-03 , DOI: 10.1021/jacs.9b12192
Guangpeng Gao , Meng Chen , Josiah Roberts _{1,

2} , Meng Feng , Chengyi Xiao , Guowei Zhang , Sean Parkin ₁ , Chad Risko _{1,

2} , Lei Zhang

Affiliation

Fullerene fragments, referred to as buckybowls, are garnering interest due to their distinctive molecular shapes and optoelectronic properties. Here we report the synthesis and characterization of a novel C70 subunit, diindeno[4,3,2,1-fghi:4',3',2',1'-opqr]perylene, that is substituted with either triethylsilyl(TES)-ethynyl or 2,4,6-triisopropylphenyl groups at the meta-positions. The resulting compounds (1 and 2) display a bowl-to-bowl inversion at room temperature. Notably, the substituent groups on the meta-positions alter both the geometric and electronic properties as well as crystal packing of the buckybowls. In contrast to the 2,4,6-triisopropylphenyl groups in 2, the TES-ethynyl groups in 1 lead to enhanced bond length alternation, resulting in weaker aromaticity of the six-membered rings of the buckybowl skeleton. 1 forms one-dimensional (1D) concave-in-convex stacking columns, and when 1 is blended with C70, the buckybowls encapsulate C70, and result in two-dimensional co-crystals. Organic field-effect transistor (OFET) measurements demonstrate that 1 displays a hole mobility of 0.31 cm2V-1s-1 and the 1-C70 co-crystal exhibits ambipolar transport characteristics with electron and hole mobilities approaching 0.40 and 0.07 cm2V-1s-1, respectively. This work demonstrates the potential of buckybowls for the development of organic semiconductors.

中文翻译：

C70 Buckybowl 的合理功能化以实现 C70:Buckybowl 共晶用于有机半导体应用

富勒烯碎片，被称为巴基碗，由于其独特的分子形状和光电特性而引起人们的兴趣。在这里，我们报告了一种新型 C70 亚基二茚并 [4,3,2,1-fghi:4',3',2',1'-opqr] 的合成和表征，它被三乙基甲硅烷基 (TES) 取代-乙炔基或2,4,6-三异丙基苯基在间位。所得化合物（1 和 2）在室温下呈现碗对碗的倒置。值得注意的是，间位上的取代基改变了巴基碗的几何和电子特性以及晶体堆积。与 2 中的 2,4,6-三异丙基苯基相比，1 中的 TES-乙炔基导致键长交替增强，导致巴克碗骨架六元环的芳香性减弱。1 形成一维 (1D) 凹凸堆积柱，当 1 与 C70 混合时，巴基碗封装 C70，并导致二维共晶。有机场效应晶体管 (OFET) 测量表明 1 显示出 0.31 cm2V-1s-1 的空穴迁移率，并且 1-C70 共晶显示出电子和空穴迁移率接近 0.40 和 0.07 cm2V-1s-1 的双极性传输特性，分别。这项工作证明了巴基碗在有机半导体开发中的潜力。31 cm2V-1s-1 和 1-C70 共晶表现出双极传输特性，电子和空穴迁移率分别接近 0.40 和 0.07 cm2V-1s-1。这项工作证明了巴基碗在有机半导体开发中的潜力。31 cm2V-1s-1 和 1-C70 共晶表现出双极传输特性，电子和空穴迁移率分别接近 0.40 和 0.07 cm2V-1s-1。这项工作证明了巴基碗在有机半导体开发中的潜力。

更新日期：2020-01-03

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