High-Performance Organic Electronic Materials by Contorting Perylene Diimides
High-Performance Organic Electronic Materials by Contorting Perylene Diimides
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DOI：
10.1021/jacs.1c11544
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发表时间：
2021-12-23
影响因子：
15
通讯作者：
Nuckolls, Colin
中科院分区：
文献类型：
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作者：
Schaack, Cedric;Evans, Austin M.;Nuckolls, Colin
二苯二亚胺(PDI)是有机电子界的主力产品。然而，包括PDI的绝大多数设计都用各种官能团取代了核心，以鼓励主要是平面的PDI之间的亲密界面接触。在过去的几年里，我们观察到了一个违反直觉的结果，即扭曲PDI的平面芳香族核心导致更高性能的光伏、光电探测器、电池和其他有机电子器件。在这个视角中，我们描述了如何将不同的扭曲模式可靠地安装到基于PDI的分子、低聚物和聚合物中。我们还描述了这些不同的扭曲如何改变观察到的PDI的光学和电学性质。例如，将PDI扭曲成碗状导致高效率的单线态裂变材料，而将PDI扭曲成螺旋烯状结构导致Cotton效应的非线性放大，最终导致迄今观察到的有机化合物最高的g-因子。最后，我们展示了这些独特的光电特性如何导致更高性能的有机电子器件。我们特别注意到这些扭曲的芳香族分子的三维结构是如何导致我们观察到的性能增强的。在整个视角中，我们强调在这一快速发展的有机材料前沿领域继续研究的机会。
Perylene diimide (PDI) is a workhorse of the organic electronics community. However, the vast majority of designs that include PDI substitute the core with various functional groups to encourage intimate cofacial contacts between largely planar PDIs. Over the past several years, we have observed the counterintuitive result that contorting the planar aromatic core of PDI leads to higher performing photovoltaics, photodetectors, batteries, and other organic electronic devices. In this Perspective, we describe how different modes of contortion can be reliably installed into PDI-based molecules, oligomers, and polymers. We also describe how these different contortions modify the observed optical and electronic properties of PDI. For instance, contorting PDIs into bowls leads to high-efficiency singlet fission materials, while contorting PDIs into helicene-like structures leads to nonlinear amplification of Cotton effects, culminating in the highest g-factors so far observed for organic compounds. Finally, we show how these unique optoelectronic properties give rise to higher performance organic electronic devices. We specifically note how the three-dimensional structure of these contorted aromatic molecules is responsible for the enhancements in performance we observe. Throughout this Perspective, we highlight opportunities for continued study in this rapidly developing organic materials frontier.