Self-assembly of redox molecules

要做的工作的性质：我们的研究计划使用有机合成来设计新型有机半导体，这些半导体可以应用于光电器件，晶体管，二极管或电池，具有可印刷，灵活，轻便和经济的电子产品的潜力。我们计划的主要目标是合成可以携带电荷的新有机构建模块;此外，我们设计新分子以促进自组装，以优化移动电荷的能力。该研究计划通过使用光吸收分子，卟啉类化合物和电荷携带分子，醌类化合物，专门针对有机光致发光（OPV）应用。有机半导体在器件中的操作的关键是在大距离上携带电荷的能力。我们的建议表明，液晶相是液体和晶体之间的中间相，使材料能够保持灵活性，同时利用晶体中的高电荷携带能力。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。我们的合成设计涉及到刚性核心的合成，该核心被赋予柔性特征的柔性链所包围。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。有序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。我们的灵感来自于对光合作用早期事件的简单看法。具体来说，自然界使用卟啉类化合物进行光捕获，醌类化合物在精致的控制和组织下作为“电子”穿梭机。我们建议通过合成手段来增强卟啉组分的捕光性能，并且我们已经证明了这些改性卟啉的成功自组装。对于醌，电子受体，积木，我们提出了几个新的核心，显示出有前途的电子亲和力，将配备自组装功能。为什么和对谁的研究是重要的：通过结合新的有机电荷携带构建块与自组装性能，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，可以迁移电荷（空穴或电子）有效，这将影响所有上述有机半导体应用。利用所提出的材料将对OPV应用产生重大影响，因此这项工作可以实现太阳能电池的灵活，经济，大面积印刷，这是大规模太阳能采用的重大障碍。此外，新的合成将是一个有益的有机化学家，新的电子和光学性质将是深刻的材料化学家和自组装是关键，以建立更好地理解分子间相互作用的超分子化学界。预期成果：首先，生产能够有效穿梭电荷的自组装材料可能是有机半导体蓬勃发展所需的一步。其次，学生将被培养为科学家，学习如何与不同的受众沟通，并成为领导者，以应对不可预见的挑战。研究领域和加拿大将如何受益：由于研究结果可能会突然改变有机化合物携带电荷的效率，加拿大可能会成为有机电子产品的新兴领导者，特别是廉价，可印刷和灵活的光电子器件。

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.