Synthetic Advances for Conjugated Material Synthesis

共轭材料合成的合成进展

• 批准号: RGPIN-2015-05533
• 负责人: Schipper, Derek
• 金额: $ 1.46万
• 依托单位: University of Waterloo
• 依托单位国家: 加拿大
• 项目类别: Discovery Grants Program - Individual
• 财政年份: 2019
• 资助国家: 加拿大
• 起止时间: 2019-01-01 至 2020-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=677312
• 关键词: Synthetic; Advances; Conjugated; Material; Synthesis

Our research is focused on tackling synthetic challenges posed in the context of conjugated organic materials. These materials are poised to make significant technological breakthroughs that will enable the advancement of flexible, lightweight, low-cost electronic devices such as photovoltaics, light emitting diodes and field-effect transistors. Innovative new synthetic capabilities will allow the design of novel molecular architectures. Ultimately, this will lead to enhanced properties for these new materials and, therefore, improved device performances. This proposal outlines three projects in pursuit of these goals.***Thiophenes represent one of the most important classes of compounds found in both conjugated polymer and small molecule organic materials. Herein, a new catalytic thiophene synthesis and polymerization for thiophene-based materials is proposed. The method should improve upon and provide complimentary reactivity to, existing methods allowing for the expedient assembly of novel thiophene-based polymeric materials. ***The biaryl motif is heavily in a variety of chemical fields and is a prevalent feature of conjugated organic materials. While traditional cross-coupling reactions prove useful synthetic tools, direct C-H bond arylation has recently emerged as a more efficient alternative. However, many drawbacks remain to be solved for direct arylation to become of truly broad synthetic utility. Herein, we propose designing catalyst/ligand structures specifically meant to solve some of these challenges by using a recent emerging mechanistic framework as a guide to catalyst design. ***Poly(p-phenylene vinylene)s (PPV) are a class of conjugated polymers which were among the first to be utilized for cutting-edge organic electronic applications and yet remain relatively unexploited. This is due in large part to limited synthetic accessibility of PPV-type polymers which not only hampers the design and testing of new derivatives but also restricts available properties of synthetically attainable polymers. Herein, we propose an alternative approach to PPV-type conjugated polymers by utilizing the C-H bond as a synthetic handle and exploiting transition-metal-catalyzed hydroarylation reactivity. The new polymerization reaction should prove valuable given the simple monomers required, its atom economical nature and ability to synthesize otherwise inaccessible polymeric structures. ***We also outline the opportunity that the proposed synthetic advances will provide an opportunity for the efficient construction of large libraries of functional conjugated organic materials. Long-term goals of this research program include utilizing the synthetic techniques to obtain previously inaccessible conjugated materials to be screened in a variety of exciting organic electronic applications.********

我们的研究重点是解决共轭有机材料的合成挑战。这些材料有望取得重大技术突破，从而推动柔性、轻量、低成本电子器件的发展，如光电子器件、发光二极管和场效应晶体管。创新的新合成能力将允许设计新的分子结构。最终，这将导致这些新材料的性能增强，从而改善设备性能。本提案概述了实现这些目标的三个项目。噻吩是共轭聚合物和小分子有机材料中最重要的一类化合物。本文提出了一种新的噻吩类材料的催化合成和聚合方法。该方法应改进现有方法并提供与现有方法互补的反应性，从而允许方便地组装新型噻吩基聚合物材料。* 联芳基基序大量存在于各种化学领域，并且是共轭有机材料的普遍特征。虽然传统的交叉偶联反应证明是有用的合成工具，但直接C-H键芳基化最近已成为更有效的替代方法。然而，许多缺点仍然有待解决的直接芳基化成为真正广泛的合成用途。在此，我们提出设计催化剂/配体结构，特别是为了解决这些挑战，通过使用最近出现的机制框架作为指导催化剂设计。* 聚（对苯撑乙烯基）（PPV）是一类共轭聚合物，是最早被用于尖端有机电子应用的聚合物之一，但仍然相对未被开发。这在很大程度上是由于PPV型聚合物的合成可及性有限，这不仅阻碍了新衍生物的设计和测试，而且还限制了合成可获得的聚合物的可用性能。在此，我们提出了一种替代的方法，PPV型共轭聚合物通过利用C-H键作为合成手柄和利用过渡金属催化的加氢芳基化反应。新的聚合反应应该被证明是有价值的，因为它需要简单的单体，它的原子经济性质和合成否则无法获得的聚合物结构的能力。* 我们还概述了提出的合成进展将为有效构建功能性共轭有机材料的大型库提供机会的机会。该研究计划的长期目标包括利用合成技术获得以前无法获得的共轭材料，以在各种令人兴奋的有机电子应用中进行筛选。