C-H Arylation Reaction: Atom Efficient and Greener Syntheses of π-Conjugated Small Molecules and Macromolecules for Organic Electronic Materials
C-H Arylation Reaction: Atom Efficient and Greener Syntheses of π-Conjugated Small Molecules and Macromolecules for Organic Electronic Materials
复制标题
DOI：
10.1021/ma401190r
复制
发表时间：
2013-10-22
期刊：
影响因子：
5.5
通讯作者：
Luscombe, Christine K.
中科院分区：
文献类型：
--
作者：
Okamoto, Ken;Zhang, Junxiang;Luscombe, Christine K.
π共轭小分子、低聚物和大分子被广泛用于制造各种有机电子器件，如有机场效应晶体管（ofet）、有机光伏（OPV）器件和有机发光二极管（oled）。需要更少的步骤、更少的有毒试剂和高活性化合物的高效合成，以从根本上更环保的方式降低材料成本。此外，具有更多官能团公差的π共轭材料的合成方法是可取的，以扩大可在此类材料中实现的性能范围。开发新的合成材料的途径既可以拓宽可探索的科学范围，又可以增加以经济上可行的方式开发出有趣的材料以纳入消费产品的可能性。一种可以影响所有这些问题的合成策略是碳氢键激活和随后的碳碳键形成（碳氢功能化）。虽然以直接芳基化为基础的方法所代表的C-H官能化在这个阶段并不像广泛使用的Stille和Suzuki方法那样发达，但它们允许使用容易获得的卤化芳香物质，并且可以消除对有毒有机锡试剂的需求。它们还有望合成以前无法获得的材料。在这个视角中，我们的目标是通过强调(1)通过交叉偶联反应制备pi共轭小分子和大分子的历史，(2)通过过渡金属催化的直接芳基化制备多功能pi共轭小分子和大分子的进展，以及(3)材料科学的范围，限制和挑战来概述这一具有挑战性的领域的现状。
pi-Conjugated small molecules, oligomers, and macromolecules are being used in the fabrication of a wide variety of organic electronic devices such as organic field-effect transistors (OFETs), organic photovoltaic (OPV) devices, and organic light-emitting diodes (OLEDs). Efficient syntheses involving fewer steps, fewer toxic reagents, and highly reactive compounds are needed to lower the cost of materials in a manner that is fundamentally more eco-friendly. Additionally, synthetic approaches for pi-conjugated materials with more functional group tolerance are desirable to expand the range of properties that can be realized in such materials. Developing new synthetic routes to materials can both broaden the scope of science that can be explored and increase the probability that interesting materials can be developed in an economically viable manner for inclusion in consumer products. One such synthetic strategy that can impact all of these issues is carbon-hydrogen bond activation and subsequent carbon-carbon bond formation (C-H functionalization). While the C-H functionalizations represented by direct arylation-based methods are not as developed as the widely used Stille and Suzuki methods at this stage, they allow for the use of readily accessible halogenated aromatic substances and can negate the need for toxic organotin reagents. They also hold promise of allowing for the synthesis of previously inaccessible materials. In this Perspective, our goal is to provide an overview of the current status in this challenging field by highlighting (1) the history of preparing pi-conjugated small molecules and macromolecules via cross-coupling reactions, (2) advances in preparation of versatile pi-conjugated small molecules and macromolecules via transition-metal-catalyzed direct arylation, and (3) the scope, limitations, and challenges for materials science.