Self-assembly of redox molecules

要做的工作性质：我们的研究项目使用有机合成来设计新型有机半导体，这些半导体可以在光伏、晶体管、二极管或电池中找到应用，具有可打印、灵活、轻便和经济的电子产品的潜力。我们项目的主要目标是合成新的有机建筑模块，可以携带电荷；此外，我们设计了新的分子来促进自组装，以优化移动电荷的能力。该研究计划专门针对有机光伏（OPVs）的应用，利用吸收光的分子，卟啉类和携带电荷的分子，醌类。器件中有机半导体工作的关键是远距离携带电荷的能力。我们的建议认为，液晶相是介于液体和晶体之间的中间相，它使材料在保持柔韧性的同时，还能利用晶体中具有的高载电荷能力。通过利用超分子化学原理，我们可以诱导分子自组装成软相，如液晶。我们的合成设计包括一个刚性核心的合成，它被赋予灵活性特性的柔性链所包围。刚性核的电子性质和尺寸与柔性链的长度和组成的平衡可以导致液晶相。有组织的材料迫使刚性核重叠，这对于允许分子间电荷传输的轨道混合至关重要。我们的灵感来源于对光合作用早期事件的简单看法。具体来说，大自然使用卟啉类物质来收集光线，醌类物质在精细的控制和组织下作为“电子”穿梭体。我们建议通过合成方法来提高卟啉组分的光捕获性能，并且我们已经成功地展示了这些修饰卟啉的自组装。对于醌类，电子受体，构建块，我们提出了几个新的核心，显示出有希望的电子亲和，将提供自组装功能。为什么以及对谁来说这项研究很重要：通过将新的有机电荷携带构建块与自组装特性相结合，我们的目标是一个破坏性的步骤，而不是增量，在新的有机材料中，可以有效地迁移电荷（空穴或电子），这将影响上述所有的有机半导体应用。开发所提出的材料将对OPV的应用产生重大影响，因此这项工作可以实现灵活、经济、大面积的太阳能电池印刷，这是大规模采用太阳能的重大障碍。此外，新的合成将有利于有机化学家，新的电子和光学性质将为材料化学家提供深刻的见解，自组装是建立对超分子化学社区分子间相互作用更好理解的关键。预期结果：首先，能够有效穿梭电荷的自组装材料的生产可能是有机半导体蓬勃发展的必要步骤。其次，学生将被训练成科学家，学习如何与不同的受众沟通，并成为应对不可预见挑战的领导者。研究领域和加拿大将如何受益：由于研究结果可能会使有机化合物携带电荷的效率发生突然变化，加拿大可能成为有机电子领域的新兴领导者，特别是廉价、可印刷和柔性的光伏设备。

Nature of the work to be done: Our research program uses organic synthesis to design novel organic semiconductors that could find applications in photovoltaics, transistors, diodes or batteries with the potential of printable, flexible, lightweight and economical electronics. The primary goal of our program is to synthesize new organic building blocks that can carry charge; in addition, we design our new molecules to promote self-assembly to optimize the ability to move charges. The research proposal targets specifically organic photovoltaics (OPVs) applications by using light-absorbing molecules, porphyrinoids, and charge carrying molecules, quinones. Essential to the operation of the organic semiconductors in devices is the ability to carry charges over large distances. Our proposal suggests liquid crystalline phases, which are intermediate phases between liquids and crystals, enable the materials to maintain flexibility yet take advantage of the high charge carrying ability found in crystals. By exploiting supramolecular chemistry principles, we can induce molecules to self-assemble into soft phases, such as liquid crystals. Our synthetic design involves the synthesis of a rigid core that is surrounded by flexible chains that impart the flexibility characteristics. The balance of the electronic properties and size of the rigid core with the length and composition of the flexible chains can lead to liquid crystalline phases. The organized materials force the rigid cores to overlap, which is critical for the mixing of orbitals that allow for intermolecular charge transport. Our inspiration is derived from a simplistic view of the early events in photosynthesis. Specifically, nature uses porphyrinoids for light harvesting and quinones as ‘electron’ shuttles under exquisite control and organization. We propose to enhance the light harvesting properties of porphyrin components by synthetic means and we have already demonstrated successful self-assembly with these modified porphyrins. For the quinones, electron acceptor, building blocks we propose several new cores that show promising electron affinities that will be furnished with self-assembling functionality. Why and to whom the research is important: By combining new organic charge carrying building blocks with self-assembling properties, we are targeting a disruptive step, as opposed to incremental, in new organic materials that can migrate charges (either holes or electrons) efficiently, which will impact all of the organic semiconductor applications described above. Exploiting the proposed materials will have a significant impact on OPV applications, such that this work could enable flexible, economical, large area printing of solar cells, which are significant roadblocks to large-scale solar energy adoption. Furthermore, the new syntheses will be a benefit to the organic chemists, the novel electronic and optical properties will be insightful for the materials chemist and the self-assembly is key to build better understanding of intermolecular interactions for the supramolecular chemistry community. Anticipated outcomes: First, the production of self-assembling materials that shuttle charges efficiently could be the step needed for organic semiconductors to flourish. Second, students will be trained as scientists and learn how to communicate with diverse audiences and become leaders to tackle unforeseen challenges. How the research field and Canada will benefit: Since the outcomes of the research could provide an abrupt change in the efficiency of organic compounds to carry charge, Canada could be an emerging leader in organic electronics, particularly photovoltaics devices that are inexpensive, printable and flexible.