Gupta Ravindra Kumar, Sudhakar Achalkumar Ammathnadu
Department of Chemistry , Indian Institute of Technology Guwahati , Guwahati 781039 , Assam , India.
Langmuir. 2019 Feb 19;35(7):2455-2479. doi: 10.1021/acs.langmuir.8b01081. Epub 2018 Jul 9.
Columnar phases formed by the stacking of disclike molecules with an intimate π-π overlap forms a 1D pathway for the anisotropic charge migration along the columns. Columnar phases have great potential in organic electronic devices to be utilized as active semiconducting layers in comparison to organic single crystals or amorphous polymers in terms of processability, ease of handling, and high charge carrier mobility. Intelligent molecular engineering of perylene and its derivatives provided access to tune the physical properties and self-assembly behavior. The columnar phase formed by perylene derivatives has great potential in the fabrication of organic electronic devices. There are several positions on the perylene molecule, which can be functionalized to tune its self-assembly, as well as optoelectronic properties. Thus, many liquid-crystalline molecules stabilizing the columnar phase, which are based on perylene tetraesters, perylene diester imides, and perylene bisimides, have been synthesized over the years. Their longitudinal and laterally extended derivatives, bay-substituted derivatives exhibiting a columnar phase, are reported. In addition, several liquid-crystalline oligomers and polymers based on perylene derivatives were also reported. All such modifications provide an option to tune the energy levels of frontier molecular orbitals with respect to the work function of the electrodes in devices and also the processability of such materials. In this feature article, we attempt to provide an overview of the molecular design developed to tune the applicable properties and self-assembly of perylene derivatives as well as recent developments related to their application in the fabrication of organic solar cells, organic light-emitting diodes, and organic field-effect transistors.
由具有紧密π-π重叠的盘状分子堆叠形成的柱状相，为沿柱的各向异性电荷迁移形成了一维路径。与有机单晶或非晶聚合物相比，柱状相在有机电子器件中作为活性半导体层具有很大潜力，在可加工性、易处理性和高电荷载流子迁移率方面表现出色。苝及其衍生物的智能分子工程为调节其物理性质和自组装行为提供了途径。苝衍生物形成的柱状相在有机电子器件制造中具有很大潜力。苝分子上有几个位置可以进行功能化，以调节其自组装以及光电性质。因此，多年来已经合成了许多基于苝四酯、苝二酯酰亚胺和苝双酰亚胺的稳定柱状相的液晶分子。报道了它们的纵向和横向扩展衍生物，即呈现柱状相的湾区取代衍生物。此外，还报道了几种基于苝衍生物的液晶低聚物和聚合物。所有这些修饰为调节前沿分子轨道的能级提供了一种选择，使其相对于器件中电极的功函数以及此类材料的可加工性。在这篇专题文章中，我们试图概述为调节苝衍生物的适用性质和自组装而开发的分子设计，以及它们在有机太阳能电池、有机发光二极管和有机场效应晶体管制造中的应用的最新进展。
